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WO2023238769A1 - Organic electroluminescent element, compound, and electronic device - Google Patents

Organic electroluminescent element, compound, and electronic device Download PDF

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Publication number
WO2023238769A1
WO2023238769A1 PCT/JP2023/020460 JP2023020460W WO2023238769A1 WO 2023238769 A1 WO2023238769 A1 WO 2023238769A1 JP 2023020460 W JP2023020460 W JP 2023020460W WO 2023238769 A1 WO2023238769 A1 WO 2023238769A1
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carbon atoms
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French (fr)
Japanese (ja)
Inventor
拓史 塩見
行俊 甚出
俊成 荻原
秀尭 星野
和真 長尾
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Idemitsu Kosan Co Ltd
Toray Industries Inc
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Idemitsu Kosan Co Ltd
Toray Industries Inc
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Priority to CN202380044420.7A priority Critical patent/CN119302067A/en
Priority to KR1020247041676A priority patent/KR20250022697A/en
Priority to US18/872,352 priority patent/US20250359477A1/en
Publication of WO2023238769A1 publication Critical patent/WO2023238769A1/en
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Definitions

  • the present invention relates to an organic electroluminescent device, a compound, and an electronic device.
  • organic electroluminescent element When a voltage is applied to an organic electroluminescent element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the emissive layer, and electrons are injected from the cathode into the emissive layer. Then, in the light emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%. Fluorescent organic EL devices that use light emission from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but an internal quantum efficiency of 25% is said to be the limit. Therefore, studies are being conducted to improve the performance of organic EL elements.
  • Patent Document 1 discloses a compound having a benzoflocarbazole ring or a benzothienocarbazole ring and a dibenzofuran ring at both ends of the para position of a linking group having an extended structure as a compound that can be used in an organic EL device. ing.
  • Examples of the performance of an organic EL element include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and life span.
  • An object of the present invention is to provide a high-performance organic electroluminescent device, a compound that can realize a high-performance organic electroluminescent device, and an electronic device equipped with the organic EL device.
  • an anode a cathode; a light-emitting layer included between the anode and the cathode,
  • the light-emitting layer includes a compound M3 represented by the following general formula (1-1) or (1-2) and a delayed fluorescent compound M2,
  • the compound M3 and the compound M2 have different structures
  • An organic electroluminescent device is provided in which the singlet energy S 1 (M3) of the compound M3 and the singlet energy S 1 (M2) of the compound M2 satisfy the relationship of the following formula (Equation 1).
  • A is a group represented by any of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
  • L 1 and L 2 are each independently, A single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms
  • Y 1 is an oxygen atom or a sulfur atom
  • R 21 to R 28 are bond to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other
  • R 100 and R 21 to R 28 that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring are each independently, hydrogen atom, halogen atom, cyano group, a substituted or unsubstituted ary
  • X 1 is an oxygen atom or a sulfur atom
  • R 11 to R 20 are bond to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other
  • R 11 to R 20 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently represented by the general formulas (1-1) and (1-2). It has the same meaning as R 21 to R 28 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, and * represents a bonding position.
  • an electronic device equipped with the organic electroluminescent element according to the above-described one aspect of the present invention.
  • a compound represented by any of the following general formulas (100-1) to (100-4) is provided.
  • A is a group represented by any of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
  • L 1 and L 2 are each independently, A single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms
  • Y 1 is an oxygen atom or a sulfur atom
  • R 21 to R 28 are bond to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other
  • R 100 and R 21 to R 28 that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring are each independently, hydrogen atom, halogen atom, cyano group, a substituted or unsubstituted
  • X 1 is an oxygen atom or a sulfur atom
  • R 11 to R 20 are bond to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other
  • R 11 to R 20 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently represented by the general formulas (100-1) to (100-4). It has the same meaning as R 21 to R 28 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, and * represents a bonding position.
  • a high-performance organic electroluminescent device it is possible to provide a high-performance organic electroluminescent device, a compound that can realize a high-performance organic electroluminescent device, and an electronic device equipped with the organic EL device.
  • FIG. 1 is a diagram showing a schematic configuration of an example of an organic electroluminescent device according to a first embodiment of the present invention.
  • FIG. 2 is a schematic diagram of an apparatus for measuring transient PL. It is a figure which shows an example of the attenuation curve of transient PL.
  • FIG. 3 is a diagram showing the relationship between the energy levels of compound M3 and compound M2 in the light emitting layer of an example of the organic electroluminescent device according to the first embodiment of the present invention. It is a figure which shows the energy level of compound M3, compound M2, and compound M1 in the light emitting layer of an example of the organic electroluminescent element based on 2nd embodiment of this invention, and the relationship of energy transfer.
  • the hydrogen atom includes isotopes having different numbers of neutrons, ie, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
  • a hydrogen atom that is, a light hydrogen atom, a deuterium atom, or Assume that tritium atoms are bonded.
  • the number of carbon atoms forming a ring refers to the number of carbon atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). represents the number of carbon atoms among the atoms.
  • a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound represents the number of carbon atoms among the atoms.
  • the carbon contained in the substituent is not included in the number of carbon atoms forming the ring.
  • the "number of ring carbon atoms" described below is the same unless otherwise specified.
  • a benzene ring has 6 carbon atoms
  • a naphthalene ring has 10 carbon atoms
  • a pyridine ring has 5 carbon atoms
  • a furan ring has 4 carbon atoms.
  • the number of ring carbon atoms in the 9,9-diphenylfluorenyl group is 13
  • the number of ring carbon atoms in the 9,9'-spirobifluorenyl group is 25.
  • the benzene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the benzene ring.
  • the number of ring carbon atoms in the benzene ring substituted with an alkyl group is 6. Further, when the naphthalene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the naphthalene ring. Therefore, the number of ring carbon atoms in the naphthalene ring substituted with an alkyl group is 10.
  • the number of ring-forming atoms refers to compounds with a structure in which atoms are bonded in a cyclic manner (e.g., monocyclic, fused ring, and ring assembly) (e.g., monocyclic compound, fused ring compound, bridged compound, carbocyclic compound). Represents the number of atoms that constitute the ring itself (compounds and heterocyclic compounds). Atoms that do not form a ring (for example, a hydrogen atom that terminates a bond between atoms that form a ring) and atoms that are included in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms.
  • the "number of ring-forming atoms" described below is the same unless otherwise specified.
  • the number of ring atoms in the pyridine ring is 6, the number of ring atoms in the quinazoline ring is 10, and the number of ring atoms in the furan ring is 5.
  • the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents is not included in the number of atoms forming the pyridine ring. Therefore, the number of ring atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is six.
  • carbon number XX to YY in the expression “substituted or unsubstituted ZZ group with carbon number XX to YY” represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in substituents.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.
  • number of atoms XX to YY in the expression “substituted or unsubstituted ZZ group with number of atoms XX to YY” represents the number of atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of atoms of substituents in case.
  • "YY" is larger than “XX”, “XX” means an integer of 1 or more, and "YY" means an integer of 2 or more.
  • an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a "substituted or unsubstituted ZZ group". represents the case where is a "substituted ZZ group".
  • "unsubstituted” in the case of "substituted or unsubstituted ZZ group” means that the hydrogen atom in the ZZ group is not replaced with a substituent.
  • the hydrogen atom in the "unsubstituted ZZ group” is a light hydrogen atom, a deuterium atom, or a tritium atom.
  • substituted in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are replaced with a substituent.
  • substitution in the case of "BB group substituted with an AA group” similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.
  • the number of ring carbon atoms in the "unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified herein. .
  • the number of ring atoms of the "unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified herein. be.
  • the number of carbon atoms in the "unsubstituted alkyl group” described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.
  • the number of carbon atoms in the "unsubstituted alkenyl group” described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
  • the number of carbon atoms in the "unsubstituted alkynyl group” described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
  • the number of ring carbon atoms in the "unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6. be.
  • the number of ring carbon atoms in the "unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18. .
  • the number of ring atoms of the "unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, more preferably 5 unless otherwise specified herein. ⁇ 18.
  • the number of carbon atoms in the "unsubstituted alkylene group” described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.
  • Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B). ) etc.
  • the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is an "unsubstituted aryl group"
  • the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group” is (Refers to the case where it is a "substituted aryl group.)
  • aryl group includes both "unsubstituted aryl group” and “substituted aryl group.”
  • “Substituted aryl group” means a group in which one or more hydrogen atoms of "unsubstituted aryl group” are replaced with a substituent.
  • Examples of the "substituted aryl group” include a group in which one or more hydrogen atoms of the "unsubstituted aryl group” in the specific example group G1A below are replaced with a substituent, and a substituted aryl group in the following specific example group G1B. Examples include: The examples of “unsubstituted aryl group” and “substituted aryl group” listed here are just examples, and the "substituted aryl group” described in this specification includes the following specific examples.
  • aryl group (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzocrysenyl group,
  • aryl group (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenyls
  • heterocyclic group is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom.
  • a “heterocyclic group” as described herein is a monocyclic group or a fused ring group.
  • a “heterocyclic group” as described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • substituted or unsubstituted heterocyclic group examples include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group ( Examples include specific example group G2B).
  • unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group” is “unsubstituted heterocyclic group”
  • substituted heterocyclic group refers to "substituted or unsubstituted heterocyclic group”
  • Heterocyclic group refers to a "substituted heterocyclic group."
  • heterocyclic group refers to "unsubstituted heterocyclic group” and “substituted heterocyclic group.” including both.
  • “Substituted heterocyclic group” means a group in which one or more hydrogen atoms of "unsubstituted heterocyclic group” are replaced with a substituent.
  • Specific examples of the "substituted heterocyclic group” include a group in which the hydrogen atom of the "unsubstituted heterocyclic group” in specific example group G2A is replaced, and examples of substituted heterocyclic groups in specific example group G2B below. Can be mentioned.
  • Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), and unsubstituted heterocyclic groups containing a sulfur atom.
  • heterocyclic group (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific example group G2A4).
  • Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), and substituted heterocyclic groups containing a sulfur atom.
  • group Specific Example Group G2B3
  • one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are substituents.
  • Includes substituted groups (Example Group G2B4).
  • ⁇ Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, Tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl
  • ⁇ Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): frill group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
  • X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
  • the monovalent heterocyclic group derived from the represented ring structure includes a monovalent group obtained by removing one hydrogen atom from these NH or CH 2 .
  • Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylylquinazolinyl group.
  • ⁇ Substituted heterocyclic group containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, A t-butyldibenzofuranyl group and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
  • ⁇ Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
  • one or more hydrogen atoms of a monovalent heterocyclic group means a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, at least one of X A and Y A is NH It means one or more hydrogen atoms selected from a hydrogen atom bonded to a nitrogen atom when the above is the case, and a hydrogen atom of a methylene group when one of X A and Y A is CH 2 .
  • Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). ).
  • an unsubstituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group” is an "unsubstituted alkyl group," and a substituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group” is (This refers to the case where it is a "substituted alkyl group.”)
  • alkyl group when it is simply referred to as an "alkyl group,” it includes both an "unsubstituted alkyl group” and a "substituted alkyl group.”
  • “Substituted alkyl group” means a group in which one or more hydrogen atoms in "unsubstituted alkyl group” are replaced with a substituent.
  • substituted alkyl group examples include groups in which one or more hydrogen atoms in the "unsubstituted alkyl group” (specific example group G3A) below are replaced with a substituent, and substituted alkyl groups (specific examples examples include group G3B).
  • the alkyl group in "unsubstituted alkyl group” means a chain alkyl group. Therefore, the "unsubstituted alkyl group” includes a linear "unsubstituted alkyl group” and a branched "unsubstituted alkyl group”.
  • ⁇ Unsubstituted alkyl group (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group.
  • ⁇ Substituted alkyl group (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group and trifluoromethyl group.
  • “Substituted or unsubstituted alkenyl group” Specific examples of the "substituted or unsubstituted alkenyl group" (specific example group G4) described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc.
  • the term "unsubstituted alkenyl group” refers to the case where "substituted or unsubstituted alkenyl group” is “unsubstituted alkenyl group”
  • “substituted alkenyl group” refers to "substituted or unsubstituted alkenyl group”).
  • alkenyl group includes both “unsubstituted alkenyl group” and “substituted alkenyl group.”
  • Substituted alkenyl group means a group in which one or more hydrogen atoms in "unsubstituted alkenyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkenyl group” include the following "unsubstituted alkenyl group” (specific example group G4A) having a substituent, and the substituted alkenyl group (specific example group G4B). It will be done.
  • ⁇ Unsubstituted alkenyl group (specific example group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group and 3-butenyl group.
  • ⁇ Substituted alkenyl group (specific example group G4B): 1,3-butandienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group and 1,2-dimethylallyl group.
  • unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group” is “unsubstituted alkynyl group."
  • "unsubstituted alkynyl group” is referred to as "unsubstituted alkynyl group.”
  • ⁇ alkynyl group'' and ⁇ substituted alkynyl group.'' "Substituted alkynyl group” means a group in which one or more hydrogen atoms in "unsubstituted alkynyl group” are replaced with a substituent.
  • Specific examples of the "substituted alkynyl group” include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group” (specific example group G5A) are replaced with a substituent.
  • Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group” described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups ( Examples include specific example group G6B).
  • unsubstituted cycloalkyl group refers to the case where "substituted or unsubstituted cycloalkyl group” is “unsubstituted cycloalkyl group”, and the term “substituted cycloalkyl group” refers to "substituted or unsubstituted cycloalkyl group”).
  • cycloalkyl group refers to the case where "substituted cycloalkyl group” is used.
  • cycloalkyl group when simply referring to “cycloalkyl group”, it refers to "unsubstituted cycloalkyl group” and “substituted cycloalkyl group”. including both.
  • Substituted cycloalkyl group means a group in which one or more hydrogen atoms in "unsubstituted cycloalkyl group” are replaced with a substituent.
  • Specific examples of the "substituted cycloalkyl group” include the following "unsubstituted cycloalkyl group” (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and a substituted cycloalkyl group. (Specific example group G6B) and the like can be mentioned.
  • cycloalkyl group (specific example group G6A): cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group and 2-norbornyl group.
  • cycloalkyl group (specific example group G6B): 4-methylcyclohexyl group.
  • G7 Specific examples of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification (specific example group G7) include: -Si(G1)(G1)(G1), -Si (G1) (G2) (G2), -Si (G1) (G1) (G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • a plurality of G2's in Si(G2) (G2) (G2) are mutually the same or different.
  • a plurality of G3's in Si(G3) (G3) are mutually the same or different.
  • - A plurality of G6's in Si(G6) (G6) (G6) are mutually the same or different.
  • G8 Specific examples of the group represented by -O-(R 904 ) described in this specification (specific example group G8) include: -O(G1), -O(G2), -O (G3) and -O (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G9 Group represented by -S-(R 905 )
  • Specific examples of the group represented by -S-(R 905 ) described in this specification include: -S (G1), -S (G2), -S (G3) and -S (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • G10 Group represented by -N(R 906 )(R 907 )
  • Specific examples of the group represented by -N(R 906 )(R 907 ) described in this specification include: -N(G1)(G1), -N(G2)(G2), -N (G1) (G2), -N (G3) (G3), and -N (G6) (G6) can be mentioned.
  • G1 is a "substituted or unsubstituted aryl group” described in specific example group G1.
  • G2 is a "substituted or unsubstituted heterocyclic group” described in specific example group G2.
  • G3 is a "substituted or unsubstituted alkyl group” described in specific example group G3.
  • G6 is a "substituted or unsubstituted cycloalkyl group” described in specific example group G6.
  • -N(G1) A plurality of G1's in (G1) are mutually the same or different.
  • -N(G2) A plurality of G2's in (G2) are the same or different.
  • -N(G3) A plurality of G3's in (G3) are mutually the same or different.
  • -N(G6) A plurality of G6's in (G6) are mutually the same or different.
  • halogen atom specifically examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
  • substituted or unsubstituted fluoroalkyl group refers to a "substituted or unsubstituted alkyl group" in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group is replaced with a fluorine atom. It also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group” are replaced with fluorine atoms (perfluoro group).
  • the number of carbon atoms in the "unsubstituted fluoroalkyl group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • “Substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of the "fluoroalkyl group” are replaced with a substituent.
  • substituted fluoroalkyl group described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl group” is further replaced with a substituent, and Also included are groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group” are further replaced with a substituent.
  • substituents of a substituent in a "substituted fluoroalkyl group” are further replaced with a substituent.
  • the "unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a fluorine atom.
  • ⁇ “Substituted or unsubstituted haloalkyl group” means that at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group” is replaced with a halogen atom. It means a group, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group” are replaced with halogen atoms.
  • the number of carbon atoms in the "unsubstituted haloalkyl group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18.
  • “Substituted haloalkyl group” means a group in which one or more hydrogen atoms of the "haloalkyl group” are replaced with a substituent.
  • the "substituted haloalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl group” is further replaced with a substituent; Also included are groups in which one or more hydrogen atoms of a substituent in the "haloalkyl group” are further replaced with a substituent.
  • Specific examples of the "unsubstituted haloalkyl group” include a group in which one or more hydrogen atoms in the "alkyl group” (specific example group G3) are replaced with a halogen atom.
  • a haloalkyl group is sometimes referred to as a halogenated alkyl group.
  • a specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkoxy group” described in specific example group G3.
  • the number of carbon atoms in the "unsubstituted alkoxy group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.
  • ⁇ “Substituted or unsubstituted alkylthio group” A specific example of the "substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkylthio group” described in specific example group G3. "unsubstituted alkyl group”. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkylthio group” is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18.
  • a specific example of the "substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryloxy group” described in specific example group G1. or an unsubstituted aryl group.
  • the number of ring carbon atoms in the "unsubstituted aryloxy group" is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • a specific example of the "substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted arylthio group” described in the specific example group G1.
  • G1 is the "substituted or unsubstituted arylthio group” described in the specific example group G1.
  • the number of ring carbon atoms in the "unsubstituted arylthio group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
  • ⁇ “Substituted or unsubstituted trialkylsilyl group” A specific example of the "substituted or unsubstituted trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a specific example It is a "substituted or unsubstituted alkyl group” described in Group G3. - A plurality of G3's in Si(G3) (G3) (G3) are mutually the same or different. The number of carbon atoms in each alkyl group of the "unsubstituted trialkylsilyl group” is from 1 to 50, preferably from 1 to 20, and more preferably from 1 to 6, unless otherwise specified herein. .
  • a specific example of the "substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), where G3 is a group described in specific example group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group” described in the specific example group G1.
  • an "aralkyl group” is a group in which the hydrogen atom of an "alkyl group” is replaced with an "aryl group” as a substituent, and is one embodiment of a “substituted alkyl group.”
  • An “unsubstituted aralkyl group” is an "unsubstituted alkyl group” substituted with an "unsubstituted aryl group”, and the number of carbon atoms in the "unsubstituted aralkyl group” is determined unless otherwise specified herein. , 7 to 50, preferably 7 to 30, more preferably 7 to 18.
  • substituted or unsubstituted aralkyl groups include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, ⁇ - Naphthylmethyl group, 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ -naphthylethyl group , 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • the substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl group, unless otherwise specified herein.
  • the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, or a phenol group, unless otherwise specified herein.
  • Nanthrolinyl group carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole -4-yl group), (9-b
  • carbazolyl group is specifically any of the following groups unless otherwise specified in the specification.
  • the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise stated in the specification.
  • dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups unless otherwise specified in the specification.
  • the substituted or unsubstituted alkyl group described herein is preferably a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t- Butyl group, etc.
  • the "substituted or unsubstituted arylene group” described in this specification refers to 2 derived from the above “substituted or unsubstituted aryl group” by removing one hydrogen atom on the aryl ring. It is the basis of valence.
  • the "substituted or unsubstituted arylene group” (specific example group G12), by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group” described in specific example group G1
  • Examples include divalent groups derived from the derivatives.
  • the "substituted or unsubstituted divalent heterocyclic group” described herein refers to the "substituted or unsubstituted heterocyclic group" described above, in which one hydrogen atom on the heterocycle is removed. It is a divalent group derived from Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include one hydrogen on the heterocycle from the "substituted or unsubstituted heterocyclic group” described in specific example group G2. Examples include divalent groups derived by removing atoms.
  • the "substituted or unsubstituted alkylene group” described in this specification refers to 2 derived from the above "substituted or unsubstituted alkyl group” by removing one hydrogen atom on the alkyl chain. It is the basis of valence.
  • a "substituted or unsubstituted alkylene group” (specific example group G14), one hydrogen atom on the alkyl chain is removed from the "substituted or unsubstituted alkyl group” described in specific example group G3. Examples include divalent groups derived from the derivatives.
  • the substituted or unsubstituted arylene group described herein is preferably a group represented by any of the following general formulas (TEMP-42) to (TEMP-68).
  • Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
  • * represents the bonding position.
  • Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
  • Formulas Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
  • * represents the bonding position.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • * represents the bonding position.
  • the substituted or unsubstituted divalent heterocyclic group described herein is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein. It is.
  • Q 1 to Q 9 are each independently a hydrogen atom or a substituent.
  • * represents the bonding position.
  • Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
  • * represents the bonding position.
  • the set of two or more adjacent R 930 is one set. is a set of R 921 and R 922 , a set of R 922 and R 923 , a set of R 923 and R 924 , a set of R 924 and R 930 , a set of R 930 and R 925 , a set of R 925 and A set of R 926 , a set of R 926 and R 927 , a set of R 927 and R 928 , a set of R 928 and R 929 , and a set of R 929 and R 921 .
  • the above-mentioned "one or more sets” means that two or more sets of the above-mentioned two or more adjacent sets may form a ring at the same time.
  • R 921 and R 922 combine with each other to form ring Q A
  • R 925 and R 926 combine with each other to form ring Q B
  • the above general formula (TEMP-103) The anthracene compound represented is represented by the following general formula (TEMP-104).
  • a set of two or more adjacent items forms a ring is not only the case where a set of "two" adjacent items are combined as in the example above, but also the case where a set of "three or more adjacent items” form a ring. This also includes the case where two sets are combined.
  • R 921 and R 922 combine with each other to form a ring Q A
  • R 922 and R 923 combine with each other to form a ring Q C
  • the three adjacent to each other (R 921 , R 922 and R 923 ) combine with each other to form a ring and are condensed to the anthracene mother skeleton.
  • anthracene compound represented by the general formula (TEMP-103) is as follows: It is represented by the general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .
  • the "single ring” or “fused ring” that is formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even if “one set of two adjacent rings” forms a “monocycle” or “fused ring,” the “monocycle” or “fused ring” is a saturated ring, or Can form unsaturated rings.
  • ring Q A and ring Q B formed in the general formula (TEMP-104) are each a “monocyclic ring” or a “fused ring.”
  • the ring Q A and the ring Q C formed in the general formula (TEMP-105) are "fused rings”.
  • Ring Q A and ring Q C in the general formula (TEMP-105) are a condensed ring due to the condensation of ring Q A and ring Q C.
  • ring Q A in the general formula (TMEP-104) is a benzene ring
  • ring Q A is a monocyclic ring.
  • ring Q A in the general formula (TMEP-104) is a naphthalene ring
  • ring Q A is a fused ring.
  • Unsaturated ring refers to an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring having an unsaturated bond in the ring structure, and a non-aromatic heterocycle having an unsaturated bond in the ring structure. At least one ring selected from the group.
  • the unsaturated bond that the unsaturated ring has in the ring structure is one or both of a double bond and a triple bond.
  • Examples of the aliphatic hydrocarbon ring having an unsaturated bond in the ring structure include cyclohexene and cyclohexadiene.
  • Examples of the non-aromatic heterocycle having an unsaturated bond in the ring structure include dihydropyran, imidazoline, pyrazoline, quinolidine, indoline, and isoindoline.
  • the "saturated ring” is at least one ring selected from an aliphatic hydrocarbon ring having no unsaturated bond and a non-aromatic heterocycle having no unsaturated bond.
  • a saturated ring has no double or triple bonds in the ring structure.
  • Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G1 are terminated with hydrogen atoms.
  • Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic group listed as a specific example in specific example group G2 is terminated with a hydrogen atom.
  • Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G6 are terminated with hydrogen atoms.
  • Form a ring means to form a ring with only a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more arbitrary atoms.
  • the ring Q A shown in the general formula (TEMP-104) formed by R 921 and R 922 bonding to each other is a carbon atom of the anthracene skeleton to which R 921 is bonded, and an anthracene bond to which R 922 is bonded. It means a ring formed by a carbon atom of the skeleton and one or more arbitrary atoms.
  • R 921 and R 922 form a ring Q A
  • the carbon atom of the anthracene skeleton to which R 921 is bonded the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms.
  • R 921 and R 922 form a monocyclic unsaturated ring
  • the ring formed by R 921 and R 922 is a benzene ring.
  • any atom is preferably at least one atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom.
  • any atom for example, in the case of a carbon atom or a nitrogen atom
  • a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent” described below.
  • the ring formed is a heterocycle.
  • "one or more arbitrary atoms" constituting a monocyclic ring or a condensed ring are preferably 2 to 15 atoms, more preferably 3 to 12 atoms.
  • a “monocycle” is preferred among “monocycle” and “fused ring.” Unless otherwise specified herein, the "unsaturated ring” is preferred between the “saturated ring” and the “unsaturated ring”. Unless otherwise stated herein, a “monocycle” is preferably a benzene ring. Unless otherwise stated herein, an “unsaturated ring” is preferably a benzene ring.
  • one or more pairs of two or more adjacent groups are “bonded with each other to form a substituted or unsubstituted monocycle” or “bonded with each other to form a substituted or unsubstituted fused ring”
  • one or more of the pairs of two or more adjacent atoms are bonded to each other to form a bond with a plurality of atoms of the parent skeleton and one or more of the 15 or more atoms.
  • a substituted or unsubstituted "unsaturated ring” is formed with at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the substituent is, for example, the "arbitrary substituent” described below.
  • Specific examples of the substituent in the case where the above-mentioned “single ring” or “fused ring” has a substituent are the substituents described in the section of "Substituent described herein” above.
  • the substituent is, for example, the "arbitrary substituent” described below.
  • the substituent in the case of "substituted or unsubstituted” (herein referred to as "arbitrary substituent")
  • arbitrary substituent For example, unsubstituted alkyl group having 1 to 50 carbon atoms, unsubstituted alkenyl group having 2 to 50 carbon atoms, unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, A group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms,
  • R 901s When two or more R 901s exist, the two or more R 901s are the same or different, When two or more R 902s exist, the two or more R 902s are the same or different, When two or more R 903s exist, the two or more R 903s are the same or different, When two or more R 904s exist, the two or more R 904s are the same or different, When two or more R 905s exist, the two or more R 905s are the same or different, When two or more R 906s exist, the two or more R 906s are the same or different, When two or more R 907s exist, the two or more R 907s are the same or different.
  • the substituent in the case of "substituted or unsubstituted” is an alkyl group having 1 to 50 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.
  • the substituent in the case of "substituted or unsubstituted” is an alkyl group having 1 to 18 carbon atoms, A group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.
  • any adjacent substituents may form a "saturated ring" or "unsaturated ring", preferably a substituted or unsubstituted saturated ring. Forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring do.
  • any substituent may further have a substituent.
  • the substituents that the arbitrary substituents further have are the same as the above arbitrary substituents. When a plurality of arbitrary substituents exist, the plurality of arbitrary substituents are the same or different from each other.
  • the numerical range expressed using "AA-BB” has the numerical value AA written before “AA-BB” as the lower limit, and the numerical value BB written after "AA-BB”. means a range that includes as an upper limit value.
  • An organic EL element includes an organic layer between an anode and a cathode.
  • This organic layer includes at least one layer composed of an organic compound.
  • this organic layer is formed by laminating a plurality of layers made of organic compounds.
  • the organic layer may further contain an inorganic compound.
  • at least one of the organic layers is a light emitting layer. Therefore, the organic layer may be composed of, for example, one light emitting layer, or may include layers that can be employed in an organic EL element.
  • Layers that can be used in organic EL devices are not particularly limited, but for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer. Examples include layers.
  • the organic EL element of this embodiment has a light emitting layer included between an anode and a cathode.
  • the organic EL element of this embodiment has an anode, a cathode, and a light emitting layer included between the anode and the cathode, and the light emitting layer has the following general formula (1-1) or (1).
  • -2) and a delayed fluorescent compound M2 the compound M3 and the compound M2 have different structures, and the singlet energy S 1 (M3) of the compound M3,
  • the singlet energy S 1 (M2) of compound M2 satisfies the relationship of the following formula (Equation 1).
  • the present inventors have proposed that the compound M3 represented by the general formula (1-1) or (1-2) (compound M3 according to the present embodiment) be included in the light-emitting layer together with the delayed fluorescent compound M2.
  • Compound M3 according to the present embodiment combines benzofuranocarbazole or benzothienocarbazole, which supplies an appropriate amount of holes to the light emitting layer, and highly durable dibenzofuran or dibenzothiophene, into meta-bonded biphenylene or ortho-bonded biphenylene having a short conjugation length. This is a compound bound via a bound biphenylene.
  • the compound M3 according to the present embodiment exhibits high triplet energy, it is possible to sufficiently confine the triplet energy of the delayed fluorescent compound. Therefore, according to this embodiment, a high-performance organic EL element can be realized. According to one aspect of this embodiment, the organic EL element emits light with high efficiency. According to one aspect of the present embodiment, the life of the organic EL element is extended.
  • FIG. 1 shows a schematic configuration of an example of an organic EL element in this embodiment.
  • the organic EL element 1 includes a transparent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
  • the organic layer 10 is configured by stacking a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order from the anode 3 side.
  • the light emitting layer 5 may contain a metal complex. It is preferable that the light emitting layer 5 does not contain a phosphorescent material (dopant material).
  • the light emitting layer 5 preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex.
  • heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
  • the light-emitting layer 5 does not contain a metal complex.
  • the light emitting layer 5 includes a delayed fluorescent compound M2 and a compound M3 represented by the general formula (1-1) or (1-2).
  • the compound M2 is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a luminescent material), and the compound M3 is preferably a host material (sometimes referred to as a matrix material). It is preferable.
  • Compound M3 may be a compound that exhibits delayed fluorescence or may be a compound that does not exhibit delayed fluorescence.
  • the light-emitting layer in this embodiment includes a compound M3 represented by the following general formula (1-1) or (1-2).
  • Compound M3 in this embodiment may be a compound that exhibits heat-activated delayed fluorescence or a compound that does not exhibit heat-activated delayed fluorescence, but is preferably a compound that does not exhibit thermally-activated delayed fluorescence.
  • A is a group represented by any of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
  • L 1 and L 2 are each independently, A single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms
  • Y 1 is an oxygen atom or a sulfur atom
  • R 21 to R 28 are bond to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other
  • R 100 and R 21 to R 28 that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring are each independently, hydrogen atom, halogen atom, cyano group, a substituted or unsubstituted ary
  • X 1 is an oxygen atom or a sulfur atom
  • R 11 to R 20 are bond to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other
  • R 11 to R 20 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently represented by the general formulas (1-1) and (1-2). It has the same meaning as R 21 to R 28 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, and * represents a bonding position.
  • compound M3 is preferably a compound represented by the general formula (1-1).
  • the compound represented by the general formula (1-1) as compound M3 is represented by the following general formula (100-1), (100-2), (100-3) or (100-5). It is expressed as
  • A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 are Each independently has the same meaning as A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 in the general formula (1-1).
  • the compound represented by the general formula (1-2) as compound M3 is the following general formula (100-4A), (100-4B), (100-4C), or (100-4D). ).
  • A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 are Each independently has the same meaning as A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 in the general formula (1-2).
  • L 1 and L 2 are each independently a single bond or a substituted or unsubstituted phenylene group. In compound M3 according to one embodiment, L 1 and L 2 are single bonds.
  • A is a group represented by the general formula (11F). In compound M3 according to one embodiment, A is a group represented by the general formula (11D).
  • X 1 is a sulfur atom. In compound M3 according to one embodiment, X 1 is an oxygen atom. In compound M3 according to one embodiment, Y 1 is an oxygen atom. In compound M3 according to one embodiment, X 1 is a sulfur atom and Y 1 is an oxygen atom. In compound M3 according to one embodiment, X 1 and Y 1 are oxygen atoms.
  • R 21 to R 28 are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group). be.
  • R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted carbazolyl group.
  • R 21 to R 28 are hydrogen atoms. In compound M3 according to one embodiment, at least one of R 21 to R 28 is a deuterium atom.
  • R 11 to R 20 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group). be.
  • R 11 to R 20 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted carbazolyl group.
  • R 11 to R 20 are hydrogen atoms.
  • at least one of R 11 to R 20 is a deuterium atom.
  • R 100 is each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).
  • R 100 each independently represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzofuranyl group.
  • R 100 is a hydrogen atom.
  • at least one of the plurality of R 100 is a deuterium atom.
  • R 100 is not a group represented by -N(Rz) 2 .
  • Compound M3 according to one embodiment is Any one selected from the group consisting of compounds represented by the general formulas (100-1) to (100-3), and compounds represented by the general formulas (100-4A) to (100-4D). It is a compound. However, in the general formulas (100-4A) to (100-4D), R 100 is preferably not a group represented by -N(Rz) 2 .
  • the compounds represented by the general formulas (100-1) to (100-3) are the same as the compounds represented by the general formulas (100-1) to (100-3) among the compounds according to the fourth embodiment. are synonymous.
  • the compounds represented by the general formulas (100-4A) to (100-4D) and in which R 100 is not a group represented by -N(Rz) 2 are the general formulas among the compounds according to the fourth embodiment. It has the same meaning as the compound represented by formula (100-4).
  • compound M3 is the only compound having singlet energy S 1 larger than singlet energy S 1 (M2) of delayed fluorescent compound M2.
  • Compound M3 of the present embodiment can be produced, for example, by the method described in Examples described below.
  • Compound M3 of the present embodiment can be produced by following the reactions described in the examples below and using known alternative reactions and raw materials that match the target product.
  • Specific examples of the compound M3 of this embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.
  • the light-emitting layer of this embodiment includes a delayed fluorescent compound M2.
  • delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.
  • Transient PL measurement is a method of irradiating a sample with a pulsed laser to excite it, and measuring the attenuation behavior (transient characteristics) of PL emission after the irradiation is stopped.
  • PL emission in a TADF material is classified into an emission component from singlet excitons generated by initial PL excitation and an emission component from singlet excitons generated via triplet excitons.
  • the lifetime of the singlet exciton generated by the first PL excitation is on the order of nanoseconds, which is very short. Therefore, the light emission from the singlet exciton attenuates quickly after irradiation with the pulsed laser.
  • delayed fluorescence decays slowly because it is emitted from singlet excitons that are generated via long-lived triplet excitons.
  • the luminescence intensity derived from delayed fluorescence can be determined.
  • FIG. 2 A schematic diagram of an exemplary apparatus for measuring transient PL is shown in FIG. An example of a method for measuring transient PL and behavior analysis of delayed fluorescence using FIG. 2 will be described.
  • the transient PL measurement device 100 in FIG. 2 includes a pulse laser section 101 capable of emitting light of a predetermined wavelength, a sample chamber 102 that accommodates a measurement sample, a spectrometer 103 that spectrally spectra the light emitted from the measurement sample, and 2. It includes a streak camera 104 for forming dimensional images, and a personal computer 105 for capturing and analyzing two-dimensional images. Note that the measurement of transient PL is not limited to the apparatus shown in FIG. 2.
  • the sample accommodated in the sample chamber 102 is obtained by forming a thin film doped with a doping material at a concentration of 12% by mass relative to the matrix material on a quartz substrate.
  • the thin film sample housed in the sample chamber 102 is irradiated with a pulsed laser from the pulsed laser section 101 to excite the doping material.
  • Emitted light is extracted in a direction 90 degrees with respect to the irradiation direction of the excitation light, the extracted light is separated into spectra by a spectroscope 103, and a two-dimensional image is formed within a streak camera 104.
  • a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spots correspond to emission intensity.
  • a thin film sample A was prepared as described above using reference compound H1 below as a matrix material and reference compound D1 below as a doping material, and transient PL measurement was performed.
  • Thin film sample B was prepared as described above using the following reference compound H2 as the matrix material and the reference compound D1 as the doping material.
  • FIG. 3 shows attenuation curves obtained from the transient PL measured for thin film sample A and thin film sample B.
  • the fluorescence intensity of the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state is determined.
  • the ratio can be estimated. In materials with delayed fluorescence, the ratio of the intensity of delayed fluorescence that decays slowly to the intensity of fluorescence that decays quickly is relatively large.
  • Prompt light emission is light emission that is observed immediately from the excited state after being excited by pulsed light (light emitted from a pulsed laser) at a wavelength that the delayed fluorescent material absorbs.
  • Delayed light emission is light emission that is not observed immediately after excitation by the pulsed light but is observed afterward.
  • the amount of prompt light emission and delay light emission and the ratio thereof can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference Document 1). Note that the device used to calculate the amount of prompt light emission and delay light emission is not limited to the device described in reference document 1 or the device described in FIG. 2.
  • a sample prepared by the following method is used to measure the delayed fluorescence of compound M2.
  • compound M2 is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption.
  • the sample solution is frozen and degassed and then sealed in a cell with a lid under an argon atmosphere, thereby making the sample solution saturated with argon and oxygen-free.
  • the fluorescence spectrum of the above sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. Using the fluorescence area intensity of both spectra, Morris et al. J. Phys. Chem. The total fluorescence quantum yield is calculated using equation (1) in 80 (1976) 969.
  • the amount of prompt light emission (immediate light emission) of the compound to be measured (compound M2 ) is preferably 0.05 or more.
  • the measurement of the amount of prompt emission and delay emission and the ratio thereof of compounds other than compound M2 is also the same as the measurement of the amount of prompt emission and delay emission of compound M2 and the ratio thereof.
  • Specific examples of the compound M2 of this embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.
  • the energy gap T 77K (M3) of compound M3 at 77 [K] is preferably larger than the energy gap T 77K (M2) of compound M2 at 77 [K]. That is, it is preferable that the relationship of the following mathematical formula (Equation 11) be satisfied. T 77K (M3)>T 77K (M2) ... (Math. 11)
  • compound M3 does not primarily emit light in the light emitting layer.
  • triplet energy is measured as follows. First, a sample is prepared by sealing a solution in which a compound to be measured is dissolved in an appropriate solvent in a quartz glass tube.
  • the heat-activated delayed fluorescent compound is preferably a compound with a small ⁇ ST.
  • ⁇ ST intersystem crossing and reverse intersystem crossing are likely to occur even in a low temperature (77 [K]) state, and excited singlet states and excited triplet states coexist.
  • the spectrum measured in the same manner as above includes light emission from both the excited singlet state and the excited triplet state, and it is difficult to clearly distinguish from which state the light is emitted.
  • the value of triplet energy is considered to be dominant. Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish that they are different in the strict sense, the value measured as follows is referred to as the energy gap T 77K . .
  • the tangent to the rise of the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values of the spectrum, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent line increases as the curve rises (ie, as the vertical axis increases). The tangent drawn at the point where the value of this slope takes the maximum value (that is, the tangent at the inflection point) is the tangent to the rise of the short wavelength side of the phosphorescence spectrum.
  • a local maximum point with a peak intensity that is 15% or less of the maximum peak intensity of the spectrum is not included in the local maximum value on the shortest wavelength side mentioned above, but is included in the maximum value of the slope that is closest to the local maximum value on the shortest wavelength side.
  • the tangent line drawn at the point where the value is taken is the tangent line to the rise of the short wavelength side of the phosphorescence spectrum.
  • an F-4500 spectrofluorometer manufactured by Hitachi High-Technologies Corporation can be used. Note that the measurement device is not limited to this, and measurement may be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.
  • Examples of the absorption spectrum measuring device include, but are not limited to, a spectrophotometer manufactured by Hitachi (device name: U3310).
  • the tangent to the falling edge of the long wavelength side of the absorption spectrum is drawn as follows.
  • the slope of this tangent line repeats decreasing and then increasing as the curve falls (that is, as the value on the vertical axis decreases).
  • the tangent line drawn at the point where the slope value takes the minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is the tangent to the fall of the long wavelength side of the absorption spectrum. Note that a maximum point with an absorbance value of 0.2 or less is not included in the maximum value on the longest wavelength side.
  • the difference (S 1 ⁇ T 77K ) between the singlet energy S 1 and the energy gap T 77K at 77 [K] is defined as ⁇ ST.
  • the difference ⁇ ST(M2) between the singlet energy S 1 (M2) of the compound M2 and the energy gap T 77K (M2) at 77[K] of the compound M2 is preferably less than 0.3 eV, more preferably Preferably it is less than 0.2 eV, more preferably less than 0.1 eV, even more preferably less than 0.01 eV. That is, it is preferable that ⁇ ST(M2) satisfy any one of the following mathematical expressions (Equation 1A) to (Equation 1D).
  • ⁇ ST(M2) S 1 (M2)-T 77K (M2) ⁇ 0.3eV
  • ⁇ ST(M2) S 1 (M2)-T 77K (M2) ⁇ 0.2eV
  • ⁇ ST (M2) S 1 (M2) - T 77K (M2) ⁇ 0.1eV
  • ⁇ ST (M2) S 1 (M2) - T 77K (M2) ⁇ 0.01 eV
  • the thickness of the light-emitting layer in the organic EL element according to this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and most preferably 10 nm or more and 50 nm or less.
  • the thickness is 5 nm or more, it is easy to form a light emitting layer and adjust the chromaticity, and when it is 50 nm or less, an increase in driving voltage is easily suppressed.
  • the content rate of the compound M2 and the compound M3 contained in the light emitting layer is preferably in the following range, for example.
  • the content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.
  • the content of compound M3 is preferably 20% by mass or more and 90% by mass or less, more preferably 40% by mass or more and 90% by mass or less, and even more preferably 40% by mass or more and 80% by mass or less. . Note that this embodiment does not exclude that the light-emitting layer includes materials other than compound M2 and compound M3.
  • the light-emitting layer may contain only one type of compound M2, or may contain two or more types of compound M2.
  • the light-emitting layer may contain only one type of compound M3, or may contain two or more types of compound M3.
  • FIG. 4 is a diagram showing an example of the relationship between the energy levels of compound M3 and compound M2 in the light emitting layer.
  • S0 represents the ground state.
  • S1(M2) represents the lowest excited singlet state of compound M2
  • T1(M2) represents the lowest excited triplet state of compound M2.
  • S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3.
  • the lowest excited triplet state T1 of compound M2 can reverse intersystem cross to the lowest excited singlet state S1 by thermal energy. be.
  • the light-emitting layer does not contain a fluorescent dopant in the lowest excited singlet state S1 (M2), which is smaller than the lowest excited singlet state S1 (M2) of compound M2, the compound Emission from the lowest excited singlet state S1 (M2) of M2 can be observed. It is believed that the internal quantum efficiency can be theoretically increased to 100% by utilizing delayed fluorescence caused by this TADF mechanism.
  • the organic EL device of this embodiment includes a delayed fluorescent compound M2 and a compound M3 (formula (1-1) or (1-2)) having a larger singlet energy than the compound M2 in the light emitting layer. It contains the represented compound M3). According to this embodiment, a high-performance organic EL element is realized. According to one aspect of this embodiment, an organic EL element that emits light with high efficiency is realized. According to one aspect of this embodiment, an organic EL element that emits light with a long life is realized. The organic EL element of this embodiment can be used in electronic devices such as display devices and light emitting devices.
  • the substrate is used as a support for the organic EL element.
  • the substrate for example, glass, quartz, plastic, etc. can be used.
  • a flexible substrate may be used.
  • the flexible substrate refers to a (flexible) substrate that can be bent, and includes, for example, a plastic substrate.
  • materials forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate.
  • an inorganic vapor-deposited film can also be used.
  • anode For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. , graphene, etc.
  • ITO indium oxide-tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide silicon oxide
  • tungsten oxide tungsten oxide
  • indium oxide containing zinc oxide graphene, etc.
  • gold Au
  • platinum Pt
  • nickel Ni
  • tungsten W
  • Cr chromium
  • Mo molybdenum
  • iron Fe
  • Co cobalt
  • Cu copper
  • palladium Pd
  • titanium Ti
  • a nitride of a metal material eg, titanium nitride
  • indium oxide-zinc oxide can be formed by a sputtering method by using a target containing 1% by mass or more and 10% by mass or less of zinc oxide relative to indium oxide.
  • indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass or more of tungsten oxide and 5% by mass or less, and 0.1% by mass or more and 1% by mass or less of zinc oxide relative to indium oxide.
  • a target it can be formed by a sputtering method.
  • it may be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, or the like.
  • the hole injection layer formed in contact with the anode is formed using a composite material that allows easy hole injection regardless of the work function of the anode.
  • materials that can be used as electrode materials for example, metals, alloys, electrically conductive compounds, mixtures thereof, and other elements belonging to Group 1 or Group 2 of the Periodic Table of Elements can be used.
  • Elements belonging to Group 1 or Group 2 of the periodic table of elements which are materials with a small work function, such as alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca), and strontium ( It is also possible to use alkaline earth metals such as Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
  • a vacuum evaporation method or a sputtering method can be used.
  • silver paste or the like a coating method, an inkjet method, etc. can be used.
  • cathode For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less).
  • cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, such as alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), and calcium (Ca). and alkaline earth metals such as strontium (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.
  • alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), and calcium (Ca).
  • alkaline earth metals such as strontium (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (
  • a vacuum evaporation method or a sputtering method can be used.
  • a coating method, an inkjet method, etc. can be used.
  • the cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the size of the work function. can do.
  • These conductive materials can be formed into films using a sputtering method, an inkjet method, a spin coating method, or the like.
  • the hole injection layer is a layer containing a substance with high hole injection properties.
  • Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, etc. can be used.
  • high molecular compounds oligomers, dendrimers, polymers, etc.
  • poly(N-vinylcarbazole) abbreviation: PVK
  • poly(4-vinyltriphenylamine) abbreviation: PVTPA
  • poly[N-(4- ⁇ N'-[4-(4-diphenylamino) phenyl]phenyl-N'-phenylamino ⁇ phenyl) methacrylamide] abbreviation: PTPDMA
  • poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] abbreviation: Polymer compounds such as Poly-TPD
  • a polymer compound to which an acid is added such as poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS) or polyaniline/poly(styrene sulfonic acid) (PAni/PSS), is used. You can also do that.
  • the hole transport layer is a layer containing a substance with high hole transport properties.
  • aromatic amine compounds such as carbazole derivatives, anthracene derivatives, etc.
  • NPB 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • TPD N,N'-bis(3-methylphenyl)-N,N'- Diphenyl-[1,1'-biphenyl]-4,4'-diamine
  • TPD 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine
  • BAFLP 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine
  • DFLDPBi 4,4',4''-tris(N,
  • the hole transport layer contains CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl] Carbazole derivatives such as -9H-carbazole (PCzPA) and anthracene derivatives such as t-BuDNA, DNA, and DPAnth may also be used.
  • PCzPA 9H-carbazole
  • anthracene derivatives such as t-BuDNA, DNA, and DPAnth
  • Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • the layer containing a substance with high hole transport properties is not limited to a single layer, and may be a stack of two or more layers made of the above substance.
  • a material with a larger energy gap is HT-2, which was used in Examples described later.
  • the electron transport layer is a layer containing a substance with high electron transport properties.
  • the electron transport layer contains 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. can be used.
  • low-molecular organic compounds include Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato) beryllium (abbreviation: BeBq 2 ), Metal complexes such as BAlq, Znq, ZnPBO, ZnBTZ, etc. can be used.
  • benzimidazole compounds can be suitably used.
  • the substances described here mainly have an electron mobility of 10 ⁇ 6 cm 2 /(V ⁇ s) or more.
  • any material other than the above may be used as the electron transport layer, as long as it has a higher electron transport property than hole transport property.
  • the electron transport layer may be composed of a single layer, or may be composed of two or more laminated layers made of the above substances.
  • a polymer compound can also be used for the electron transport layer.
  • PF-Py poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)]
  • PF-BPy poly[(9,9-dioctylfluorene-2, ,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)]
  • PF-BPy poly[(9,9-dioctylfluorene-2, ,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)]
  • the electron injection layer is a layer containing a substance with high electron injection properties.
  • the electron injection layer contains lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiOx), etc.
  • Alkali metals, alkaline earth metals, or compounds thereof can be used.
  • a material containing an alkali metal, an alkaline earth metal, or a compound thereof in a substance having electron transport properties specifically, a material containing magnesium (Mg) in Alq, etc. may be used. Note that in this case, electron injection from the cathode can be performed more efficiently.
  • a composite material made of a mixture of an organic compound and an electron donor may be used for the electron injection layer.
  • Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor.
  • the organic compound is preferably a material that is excellent in transporting generated electrons, and specifically, for example, the above-mentioned substances (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer are used. be able to.
  • the electron donor may be any substance that exhibits electron-donating properties to organic compounds. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • alkali metal oxides and alkaline earth metal oxides are preferable, and examples thereof include lithium oxide, calcium oxide, barium oxide, and the like. Additionally, Lewis bases such as magnesium oxide can also be used. Moreover, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.
  • TTF tetrathiafulvalene
  • Methods for forming each layer of the organic EL element of this embodiment are not limited to those specifically mentioned above, but dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating, and spin Known methods such as coating methods, dipping methods, flow coating methods, wet film forming methods such as inkjet methods can be employed.
  • each organic layer of the organic EL element of this embodiment is not limited except as specifically mentioned above, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur; Since an applied voltage is required and efficiency deteriorates, the range of from several nm to 1 ⁇ m is usually preferable.
  • the organic EL device of the second embodiment differs from the organic EL device of the first embodiment in that the light emitting layer further contains a fluorescent compound M1. Other points are similar to the first embodiment.
  • the light-emitting layer includes a compound M3 represented by the general formula (1-1) or (1-2), a delayed fluorescent compound M2, and a fluorescent compound M1. including.
  • compound M1 is preferably a dopant material
  • compound M2 is preferably a host material
  • compound M3 is preferably a host material.
  • One of compound M2 and compound M3 may be referred to as a first host material, and the other may be referred to as a second host material.
  • Compound M1 of this embodiment contains a fluorescent compound M1.
  • Compound M1 of this embodiment is not a phosphorescent metal complex. It is preferable that the compound M1 of this embodiment is not a heavy metal complex. Moreover, it is preferable that the compound M1 of this embodiment is not a metal complex. Moreover, it is preferable that the compound M1 of this embodiment is a compound that does not exhibit heat-activated delayed fluorescence.
  • a fluorescent material can be used as the compound M1 of this embodiment.
  • Specific examples of the fluorescent material include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, and bisarylaminopyrene derivatives.
  • Chrysene derivatives aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing a boron atom, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, Examples include metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.
  • compound M1 When compound M1 is a fluorescent compound, compound M1 preferably emits light with a maximum peak wavelength of 400 nm or more and 700 nm or less.
  • the maximum peak wavelength refers to the maximum emission intensity in the measured fluorescence spectrum of a toluene solution in which the target compound is dissolved at a concentration of 10 -6 mol/liter or more and 10 -5 mol/liter or less.
  • the peak wavelength of the fluorescence spectrum is used as the measuring device.
  • Compound M1 preferably emits red or green light.
  • red light emission refers to light emission in which the maximum peak wavelength of the fluorescence spectrum is within the range of 600 nm or more and 660 nm or less.
  • the maximum peak wavelength of compound M1 is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and even more preferably 610 nm or more and 630 nm or less.
  • green light emission refers to light emission in which the maximum peak wavelength of the fluorescence spectrum is within the range of 500 nm or more and 560 nm or less.
  • the maximum peak wavelength of compound M1 is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and still more preferably 510 nm or more and 540 nm or less.
  • blue light emission refers to light emission in which the maximum peak wavelength of the fluorescence spectrum is within the range of 430 nm or more and 480 nm or less.
  • the maximum peak wavelength of compound M1 is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.
  • the maximum peak wavelength of light emitted from an organic EL element is measured as follows.
  • a spectral radiance spectrum is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta) when a voltage is applied to the organic EL element so that the current density is 10 mA/cm 2 .
  • the peak wavelength of the emission spectrum at which the emission intensity becomes maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).
  • compound M1 is preferably a compound represented by the following general formula (2A).
  • compound M1 is preferably a compound that emits light with a maximum peak wavelength of 500 nm or more and 560 nm or less.
  • the Za ring, Zb ring, and Zc ring are each independently, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms, Ra combines with the Za ring or the Zb ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle, Rb combines with the Za ring or the Zc ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle,
  • the above-mentioned Ra and Rb which do not form a substituted or unsubstituted heterocycle are each independently, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms
  • the compound M1 is a compound represented by the following general formula (D11).
  • the compound represented by the general formula (2A) is also preferably a compound represented by the following general formula (D11).
  • Rb has the same meaning as Rb in the general formula (2A), X 1 is CR 1 or a nitrogen atom, X 2 is CR 2 or a nitrogen atom, X 3 is CR 3 or a nitrogen atom, X 4 is CR 4 or a nitrogen atom, X 5 is CR 5 or a nitrogen atom, X 6 is CR 6 or a nitrogen atom, X 7 is CR 7 , a nitrogen atom, or a carbon atom bonded to X 8 with a single bond, X 8 is CR 8 , a nitrogen atom, or a carbon atom bonded to X 7 with a single bond, X 9 is CR 9 or a nitrogen atom, X 10 is CR 10 or a nitrogen atom, X 11 is CR 11 or a nitrogen atom, X 12 is CR 12 or a nitrogen atom, Q is CR Q or a nitrogen atom, One or more sets of adjacent two or more of R 1
  • the compound represented by the general formula (D11) is also preferably represented by the following general formula (D13).
  • R 1 to R 3 , R 5 to R 13 and R Q are each independently synonymous with R 1 to R 3 , R 5 to R 13 and R Q in the general formula (D11),
  • One or more sets of two or more adjacent ones of R A1 to R A4 are bond to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other
  • R A1 to R A4 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted fused ring are each independently: hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms
  • the compound represented by the general formula (D11) is also preferably represented by the following general formula (D13A).
  • R 1 , R 3 , R 5 to R 13 , R Q and R A1 to R A4 each independently represent R 1 , R 3 , R 5 in the general formula (D13) ⁇ R 13 , R Q and R A1 ⁇ R A4 are synonymous,
  • One or more sets of two or more adjacent ones of R A5 to R A9 are bond to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
  • R A5 to R A9 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring each independently represent the substituted or unsubstituted ring in the general formula (D13). It has the same meaning as R A1 to R A4 that do not form a single ring and do not form a substituted or unsubstitute
  • the set consisting of R 5 and R 6 may be bonded to each other to form a substituted or unsubstituted monocycle, or may be bonded to each other to form a substituted or unsubstituted monocycle. They form unsubstituted fused rings or do not bond to each other.
  • R 1 to R 13 and R Q are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, It is also preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
  • R 1 to R 13 and R Q are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, It is also preferably a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.
  • R 1 to R 3 , R 5 to R 13 , R Q and R A1 to R A9 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, It is also preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
  • R 1 to R 3 , R 5 to R 13 , R Q and R A1 to R A9 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, It is also preferably a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.
  • the compound represented by the general formula (D11) is also preferably represented by the following general formula (D14).
  • R 2 , R 6 , R 13 , R Q and R A2 are each independently, hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, A substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.
  • R 13 and R Q are each independently, Substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted phenyl group, It is preferably a substituted or unsubstituted naphthyl group or a substituted or unsubstituted dibenzofuranyl group.
  • R 6 and R A2 are each independently preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • the compound M1 is a compound represented by the following general formula (16).
  • the compound represented by the general formula (2A) is also preferably a compound represented by the following general formula (16).
  • R 161 to R 177 are bond to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, R 161 to R 177 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted fused ring are each independently: hydrogen atom, Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted
  • R 161 to R 177 are each independently, hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, It is preferably a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • At least one of R 168 to R 170 is It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
  • R 161 to R 177 are each independently, It is preferably a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • R 161 to R 177 are also preferably hydrogen atoms.
  • the multiple R X1s are the same or different
  • the plurality of R X2s are the same or different from each other
  • the plurality of R X3s exist
  • the plurality of R X3s are the same or different from each other
  • the plurality of R X4s are the same or different from each other.
  • a set consisting of R 161 and R 162 A set consisting of R 165 and R 166 , It is also preferred that at least one of the group consisting of R 172 and R 173 and the group consisting of R 176 and R 177 combine with each other to form a ring represented by the general formula (16A).
  • the compound represented by the general formula (16) is also preferably a compound represented by the following general formula (161).
  • R 161 to R 164 , R 167 to R 171 , R 174 to R 177 and R X1 to R X4 each independently represent R 161 to R 164 in the general formula (16). , R 167 to R 171 , R 174 to R 177 and R X1 to R X4 in the general formula (16A) above.
  • the compound represented by the general formula (16) is also preferably a compound represented by the following general formula (162).
  • R 161 to R 163 , R 168 to R 170 and R 175 to R 177 are each independently R 161 to R 163 , R 168 to R 170 in the general formula (16) and R 175 to R 177. )
  • the compound represented by the general formula (16) is also preferably a compound represented by the following general formula (163).
  • R 162 , R 169 and R 176 each independently have the same meaning as R 162 , R 169 and R 176 in the general formula (16).
  • Compound M1 can be produced by a known method.
  • the singlet energy S 1 (M3) of the compound M3 is preferably larger than the singlet energy S 1 (M1) of the compound M1.
  • the singlet energy S 1 (M3) of compound M3, the singlet energy S 1 (M2) of compound M2, and the singlet energy S 1 (M1) of compound M1 satisfy the relationship of the following formula (Equation 2A). It is preferable. S 1 (M3)>S 1 (M2)>S 1 (M1)...(Math 2A)
  • the fluorescent compound M1 mainly emits light in the light emitting layer.
  • the organic EL element of this embodiment preferably emits red light or green light.
  • the content of the compound M3, compound M2, and compound M1 contained in the light-emitting layer is preferably within the following range, for example.
  • the content of compound M3 is preferably 10% by mass or more and 80% by mass or less.
  • the content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.
  • the content of compound M1 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and 0.01% by mass or more and 1% by mass or less.
  • the upper limit of the total content of compound M3, compound M2, and compound M1 in the light emitting layer is 100% by mass.
  • the light-emitting layer includes materials other than compound M3, compound M2, and compound M1.
  • the light-emitting layer may contain only one type of compound M3, or may contain two or more types of compound M3.
  • the light-emitting layer may contain only one type of compound M2, or may contain two or more types of compound M2.
  • the light emitting layer may contain only one type of compound M1, or may contain two or more types of compound M1.
  • FIG. 5 is a diagram showing an example of the relationship between the energy levels of compound M3, compound M2, and compound M1 in the light emitting layer.
  • S0 represents the ground state.
  • S1 (M1) represents the lowest excited singlet state of compound M1
  • T1 (M1) represents the lowest excited triplet state of compound M1.
  • S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2.
  • S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3.
  • the organic EL device of the second embodiment includes a delayed fluorescent compound M2 and a compound M3 having a larger singlet energy than the compound M2 (in the general formula (1-1) or (1-2)) in the light emitting layer. Compound M3) and compound M1 having singlet energy smaller than delayed fluorescent compound M2. According to the second embodiment, a high-performance organic EL element is realized. According to one aspect of the second embodiment, an organic EL element that emits light with high efficiency is realized. According to one aspect of the second embodiment, an organic EL element that emits light with a long life is realized.
  • the organic EL element of the second embodiment can be used in electronic devices such as display devices and light emitting devices.
  • the electronic device according to this embodiment is equipped with the organic EL element according to any of the embodiments described above.
  • Examples of electronic devices include display devices and light emitting devices.
  • Examples of display devices include display components (eg, organic EL panel modules, etc.), televisions, mobile phones, tablets, personal computers, and the like.
  • Examples of the light emitting device include lighting, vehicle lamps, and the like.
  • the compound according to the fourth embodiment is a compound represented by any of the following general formulas (100-1) to (100-4).
  • the compounds represented by the following general formulas (100-1) to (100-3) are the compounds represented by the general formula (1-1) explained in the first embodiment. This is one aspect of and has the same meaning as the compounds represented by general formulas (100-1) to (100-3) described in the first embodiment.
  • the compound represented by the following general formula (100-4) is one embodiment of the compound represented by the general formula (1-2) explained in the first embodiment, It has the same meaning as the compound represented by the general formulas (100-4A) to (100-4D) described in the first embodiment (provided that R 100 is not a group represented by -N(Rz) 2 ) .
  • A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 each independently represent the formula (1-1) It has the same meaning as A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 in.
  • A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 each independently represent A, L 1 in the general formula (1-2), It has the same meaning as L 2 , Y 1 , R 21 to R 28 and R 100 , however, in the general formula (100-4), R 100 is not a group represented by -N(Rz) 2 .
  • * represents the bonding position with any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded.
  • the compound according to the fourth embodiment is preferably a compound represented by the general formula (100-1), the general formula (100-2), or the general formula (100-3).
  • L 1 and L 2 are each independently a single bond or a substituted or unsubstituted phenylene group. In one aspect of the compound according to the fourth embodiment, L 1 and L 2 are single bonds. In one aspect of the compound according to the fourth embodiment, A is a group represented by the general formula (11F). In one aspect of the compound according to the fourth embodiment, A is a group represented by the general formula (11D). In one aspect of the compound according to the fourth embodiment, X 1 is a sulfur atom. In one aspect of the compound according to the fourth embodiment, X 1 is an oxygen atom. In one aspect of the compound according to the fourth embodiment, Y 1 is an oxygen atom. In one aspect of the compound according to the fourth embodiment, X 1 is a sulfur atom, and Y 1 is an oxygen atom. In one aspect of the compound according to the fourth embodiment, X 1 and Y 1 are oxygen atoms.
  • R 21 to R 28 are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms). phenyl group).
  • R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group.
  • R 21 to R 28 are hydrogen atoms.
  • at least one of R 21 to R 28 is a deuterium atom.
  • R 11 to R 20 are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms). phenyl group).
  • R 11 to R 20 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted carbazolyl group. It is. In one aspect of the compound according to the fourth embodiment, R 11 to R 20 are hydrogen atoms. In one aspect of the compound according to the fourth embodiment, at least one of R 11 to R 20 is a deuterium atom.
  • R 100 is each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group) It is.
  • R 100 is each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or an unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a trimethylsilyl group.
  • R 100 is a hydrogen atom.
  • at least one of the plurality of R 100 is a deuterium atom.
  • a high-performance organic EL element can be realized.
  • an organic EL element that emits light with high efficiency can be realized.
  • an organic EL element that emits light with a long life can be realized.
  • the compound of the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.
  • An organic EL device that is an aspect of the fourth embodiment uses the compound of the fourth embodiment (a compound represented by any one of the general formulas (100-1) to (100-4)) as an anode and a cathode. This is an organic EL element included in one of the organic layers arranged between them.
  • An organic EL device that is an aspect of the fourth embodiment includes a compound represented by the general formula (100-1), the general formula (100-2), or the general formula (100-3) at the anode and This is an organic EL element that is included in one of the organic layers arranged between cathodes.
  • the compound of the fourth embodiment is a compound that can realize a high-performance organic EL device. Therefore, the organic EL element that is one aspect of the fourth embodiment has high performance.
  • the organic EL element that is one aspect of the fourth embodiment emits light with high efficiency.
  • the organic EL element that is one aspect of the fourth embodiment emits light with a long lifetime.
  • Specific examples of the compound according to the fourth embodiment include, for example, the same compound as the compound exemplified as compound M3 in the first embodiment. However, the present invention is not limited to these specific examples of compounds.
  • the organic EL element material of the fifth embodiment contains the compound of the fourth embodiment. According to the organic EL element material of the fifth embodiment, a high-performance organic EL element and electronic device can be realized.
  • the organic EL element material of the sixth embodiment may further contain other compounds. When the organic EL element material of the sixth embodiment further contains other compounds, the other compounds may be solid or liquid.
  • the number of light emitting layers is not limited to one layer, and a plurality of light emitting layers may be stacked.
  • an organic EL element has a plurality of light emitting layers, it is sufficient that at least one light emitting layer satisfies the conditions described in the above embodiment.
  • the other light-emitting layer may be a fluorescent-type light-emitting layer or a phosphorescent-type light-emitting layer that utilizes light emission due to electronic transition directly from a triplet excited state to a ground state.
  • the organic EL element has a plurality of light emitting layers
  • these light emitting layers may be provided adjacent to each other, or a so-called tandem type organic EL element may be provided in which a plurality of light emitting units are stacked with an intermediate layer interposed therebetween. It may also be an EL element.
  • a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light emitting layer.
  • the barrier layer is disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons.
  • the barrier layer transports electrons and holes reach the layer on the cathode side (e.g., electron transport layer) than the barrier layer. prevent you from doing
  • the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light emitting layer and the electron transport layer.
  • the barrier layer transports holes and electrons are transferred to a layer on the anode side (for example, a hole transport layer) than the barrier layer. prevent it from reaching.
  • the organic EL element includes a hole transport layer
  • a barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. Excitons generated in the light emitting layer are prevented from moving to layers closer to the electrode than the barrier layer (for example, an electron transport layer, a hole transport layer, etc.). It is preferable that the light-emitting layer and the barrier layer are bonded to each other.
  • the compounds used for manufacturing the organic EL device of the comparative example are shown below.
  • Example 1 A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130 nm. The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum evaporation device, and first, compound HT-1 and compound HA were added to cover the transparent electrode on the side on which the transparent electrode lines were formed. was co-evaporated to form a hole injection layer with a thickness of 10 nm.
  • the concentration of compound HT-1 in the hole injection layer was 97% by mass, and the concentration of compound HA was 3% by mass.
  • compound HT-1 was deposited on the hole injection layer to form a hole transport layer with a thickness of 90 nm.
  • compound HT-2 was deposited on this hole transport layer to form an electron barrier layer with a thickness of 30 nm.
  • a fluorescent compound GD-1 which is a compound M1
  • a delayed fluorescent compound TADF-1 which is a compound M2
  • a compound M3-1 which is a compound M3 are co-evaporated.
  • a light emitting layer with a thickness of 40 nm was formed.
  • the concentration of compound GD-1 in the light emitting layer was 0.6% by mass, the concentration of compound TADF-1 was 25% by mass, and the concentration of compound M3-1 was 74.4% by mass.
  • compound ET-1 was deposited on this light emitting layer to form a hole blocking layer with a thickness of 5 nm.
  • compound ET-2 and compound Liq were co-deposited on this hole blocking layer to form an electron transport layer with a thickness of 35 nm.
  • the concentration of compound ET-2 in the electron transport layer was 50% by mass, and the concentration of compound Liq was 50% by mass. Note that Liq is an abbreviation for (8-Quinolinolato)lithium.
  • ytterbium (Yb) was deposited on this electron transport layer to form an electron injection electrode (cathode) with a thickness of 1 nm.
  • metal aluminum (Al) was deposited on this electron injection electrode to form a metal Al cathode with a film thickness of 80 nm.
  • the element structure of the organic EL element of Example 1 is schematically shown as follows.
  • the number expressed as a percentage (97%: 3%) indicates the proportion (mass%) of compound HT-1 and compound HA in the hole injection layer, and the number expressed as a percentage (74.4%) :25%:0.6%) indicates the proportion (mass%) of compound M3, compound M2, and compound M1 in the light emitting layer, and the number expressed as a percentage (50%:50%) indicates the proportion of the compound M3, compound M2, and compound M1 in the electron transport layer.
  • the ratio (mass%) of ET-2 and compound Liq is shown.
  • Example 2-3 The organic EL devices according to Examples 2 to 3 were produced in the same manner as in Example 1, except that the compound M3-1 used in Example 1 was changed to the compound listed in Table 1.
  • Comparative example 1 An organic EL device according to Comparative Example 1 was produced in the same manner as in Example 1, except that the compound M3-1 used in Example 1 was changed to the compound listed in Table 1.
  • Example 4 In the organic EL device according to Example 4, the concentration of compound TADF-1 in the light emitting layer of Example 1 was changed to the concentration listed in Table 1, and the concentration of compound M3-1 was changed to 69.4% by mass (wt%). ) was produced in the same manner as in Example 1, except for changing.
  • Example 5-6 The organic EL devices according to Examples 5 and 6 were produced in the same manner as in Example 4, except that the compound M3-1 used in Example 4 was changed to the compound listed in Table 1.
  • Comparative example 2 An organic EL device according to Comparative Example 2 was produced in the same manner as in Example 4, except that the compound M3-1 used in Example 4 was changed to the compound listed in Table 1.
  • EQE (relative value) (EQE of each example/EQE of comparative example 1) x 100... (Math 1X)
  • EQE (relative value) (EQE of each example/EQE of comparative example 2) x 100... (Math 2X)
  • the spectral radiance spectrum was measured using a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to the device so that the current density was 10 mA/cm 2 .
  • the maximum peak wavelength ⁇ p (unit: nm) was determined from the obtained spectral radiance spectrum.
  • CIE1931 chromaticity CIE1931 chromaticity coordinates (x, y) were measured using a spectral radiance meter CS-2000 (manufactured by Konica Minolta) when a voltage was applied to the organic EL element such that the current density of the element was 10 mA/cm 2 .
  • the organic EL devices of Examples 1 to 3 include the compound M3 represented by the general formula (1-1), the delayed fluorescent compound M2, and the fluorescent compound M1 in the light emitting layer. Compared to the organic EL device of Comparative Example 1 in which M3 was replaced with compound Ref-1, it emitted light with high efficiency. Further, the organic EL devices of Examples 4 to 6 containing the compound M3 represented by the general formula (1-1), the delayed fluorescent compound M2, and the fluorescent compound M1 in the light emitting layer, Compared to the organic EL device of Comparative Example 2 in which Compound M3 was replaced with Compound Ref-1, it emitted light with high efficiency and had a longer life.
  • the fluorescence spectrum of the above sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. Using the fluorescence area intensity of both spectra, Morris et al. J. Phys. Chem. The total fluorescence quantum yield was calculated using equation (1) in 80 (1976) 969. Prompt light emission (immediate light emission) that is observed immediately from the excited state after being excited by pulsed light (light emitted from a pulsed laser) with a wavelength that the compound TADF-1 absorbs, and prompt light emission that is immediately observed after the excitation.
  • pulsed light light emitted from a pulsed laser
  • Delayed fluorescent light emission in this embodiment means that the amount of delayed light emission (delayed light emission) is 5% or more of the amount of prompt light emission (immediate light emission). Specifically, when the amount of prompt light emission (immediate light emission) is X P and the amount of delay light emission (delayed light emission) is X D , the value of X D /X P is 0.05 or more. means. The amount of prompt light emission and delay light emission and the ratio thereof can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference Document 1).
  • the device used to calculate the amount of prompt light emission and delay light emission is not limited to the device described in reference document 1 or the device described in FIG. 2.
  • the amount of delayed light emission was 5% or more of the amount of prompt light emission (immediate light emission).
  • the value of X D /X P was 0.05 or more.
  • T 77K of the compound to be measured was measured by the method for measuring the energy gap T 77K described in "Relationship between triplet energy and energy gap at 77 [K]" above. Further, ⁇ ST was confirmed from the measurement results of T 77K and the value of the singlet energy S 1 mentioned above.
  • the ⁇ ST of compound GD-1 was 0.40 eV.
  • ⁇ Maximum peak wavelength ⁇ of compound The maximum peak wavelength ⁇ of the compound was measured by the following method. A 5 ⁇ mol/L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300K). In this example, the emission spectrum was measured using a spectrophotometer manufactured by Hitachi (device name: F-7000). Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum was defined as the maximum peak wavelength ⁇ .
  • reaction product was purified by silica gel chromatography and recrystallized using toluene to obtain compound M3-1 (0.85 g, yield 24%). It was identified as compound M3-1 by LC-MS analysis.
  • Organic EL element 2... Substrate, 3... Anode, 4... Cathode, 5... Light emitting layer, 6... Hole injection layer, 7... Hole transport layer, 8... Electron transport layer, 9... Electron injection layer.

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Abstract

An organic electroluminescent element (1) has an anode (3), a cathode (4), and a light-emitting layer (5) provided between the anode (3) and the cathode (4). The light-emitting layer (5) contains a compound M3 represented by general formula (1-1) or (1-2) and a delayed fluorescent compound M2. The structure of the compound M3 is different from that of the compound M2, and the singlet energy S1 (M3) of the compound M3 and the singlet energy S1 (M2) of the compound M2 satisfy the relationship in the mathematical expression (expression 1) below.　In general formulas (1-1) and (1-2), A is a group represented by general formula (11A), etc., L1 and L2 are each independently a single bond or a substituted or unsubstituted arylene group, and Y1 is an oxygen atom or a sulfur atom.　(Numerical formula 1): S1(M3)>S1(M2)

Description

有機エレクトロルミネッセンス素子、化合物、及び電子機器Organic electroluminescent devices, compounds, and electronic devices

　本発明は、有機エレクトロルミネッセンス素子、化合物、及び電子機器に関する。 The present invention relates to an organic electroluminescent device, a compound, and an electronic device.

　有機エレクトロルミネッセンス素子（以下、「有機ＥＬ素子」という場合がある。）に電圧を印加すると、陽極から正孔が発光層に注入され、また陰極から電子が発光層に注入される。そして、発光層において、注入された正孔と電子とが再結合し、励起子が形成される。このとき、電子スピンの統計則により、一重項励起子が２５％の割合で生成し、及び三重項励起子が７５％の割合で生成する。
　一重項励起子からの発光を用いる蛍光型の有機ＥＬ素子は、携帯電話及びテレビ等のフルカラーディスプレイへ応用されつつあるが、内部量子効率２５％が限界といわれている。そのため、有機ＥＬ素子の性能を向上するための検討が行われている。 When a voltage is applied to an organic electroluminescent element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the emissive layer, and electrons are injected from the cathode into the emissive layer. Then, in the light emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.
Fluorescent organic EL devices that use light emission from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but an internal quantum efficiency of 25% is said to be the limit. Therefore, studies are being conducted to improve the performance of organic EL elements.

　また、一重項励起子に加えて三重項励起子を利用し、有機ＥＬ素子をさらに効率的に発光させることが期待されている。このような背景から、熱活性化遅延蛍光（以下、単に「遅延蛍光」という場合がある。）を利用した高効率の蛍光型の有機ＥＬ素子が提案され、研究がなされている。
　例えば、ＴＡＤＦ（Ｔｈｅｒｍａｌｌｙ　Ａｃｔｉｖａｔｅｄ　Ｄｅｌａｙｅｄ　Ｆｌｕｏｒｅｓｃｅｎｃｅ、熱活性化遅延蛍光）機構（メカニズム）が研究されている。このＴＡＤＦメカニズムは、一重項準位と三重項準位とのエネルギー差（ΔＳＴ）の小さな材料を用いた場合に、三重項励起子から一重項励起子への逆項間交差が熱的に生じる現象を利用するメカニズムである。熱活性化遅延蛍光については、例えば、『安達千波矢編、「有機半導体のデバイス物性」、講談社、２０１２年４月１日発行、２６１－２６８ページ』に記載されている。 Furthermore, it is expected that triplet excitons will be used in addition to singlet excitons to cause organic EL devices to emit light more efficiently. Against this background, highly efficient fluorescent organic EL devices using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and researched.
For example, the TADF (Thermally Activated Delayed Fluorescence) mechanism has been studied. In this TADF mechanism, when a material with a small energy difference (ΔST) between the singlet and triplet levels is used, reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally. It is a mechanism that utilizes phenomena. Thermal activation delayed fluorescence is described, for example, in "Chihaya Adachi, ed., "Device Properties of Organic Semiconductors," Kodansha, published April 1, 2012, pages 261-268."

　例えば、特許文献１においては、有機ＥＬ素子の性能向上を図るための検討がなされている。特許文献１には、有機ＥＬ素子に用いることのできる化合物として、伸長構造を有する連結基のパラ位の両端に、ベンゾフロカルバゾール環又はベンゾチエノカルバゾール環と、ジベンゾフラン環とを有する化合物が開示されている。
　有機ＥＬ素子の性能としては、例えば、輝度、発光波長、色度、発光効率、駆動電圧、及び寿命が挙げられる。 For example, in Patent Document 1, studies are made to improve the performance of organic EL elements. Patent Document 1 discloses a compound having a benzoflocarbazole ring or a benzothienocarbazole ring and a dibenzofuran ring at both ends of the para position of a linking group having an extended structure as a compound that can be used in an organic EL device. ing.
Examples of the performance of an organic EL element include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and life span.

国際公開第２０２０／１２２１１８号International Publication No. 2020/122118

　ＴＡＤＦメカニズムを利用した有機ＥＬ素子において、更なる性能の向上が求められている。 Further improvement in performance is required in organic EL devices that utilize the TADF mechanism.

　本発明の目的は、高性能な有機エレクトロルミネッセンス素子、高性能な有機エレクトロルミネッセンス素子を実現できる化合物、及び当該有機ＥＬ素子を搭載した電子機器を提供することである。 An object of the present invention is to provide a high-performance organic electroluminescent device, a compound that can realize a high-performance organic electroluminescent device, and an electronic device equipped with the organic EL device.

　本発明の一態様によれば、
　陽極と、
　陰極と、
　前記陽極と前記陰極との間に含まれる発光層と、を有し、
　前記発光層は、下記一般式（１－１）または（１－２）で表される化合物Ｍ３と、遅延蛍光性の化合物Ｍ２と、を含み、
　前記化合物Ｍ３と前記化合物Ｍ２とは構造が異なり、
　前記化合物Ｍ３の一重項エネルギーＳ１（Ｍ３）と、前記化合物Ｍ２の一重項エネルギーＳ１（Ｍ２）とが、下記数式（数１）の関係を満たす、有機エレクトロルミネッセンス素子が提供される。
　　　Ｓ１（Ｍ３）＞Ｓ１（Ｍ２）　　　（数１） According to one aspect of the invention,
an anode;
a cathode;
a light-emitting layer included between the anode and the cathode,
The light-emitting layer includes a compound M3 represented by the following general formula (1-1) or (1-2) and a delayed fluorescent compound M2,
The compound M3 and the compound M2 have different structures,
An organic electroluminescent device is provided in which the singlet energy S 1 (M3) of the compound M3 and the singlet energy S 1 (M2) of the compound M2 satisfy the relationship of the following formula (Equation 1).
S 1 (M3)>S 1 (M2) (Math. 1)

（前記一般式（１－１）及び（１－２）において、
　Ａは、下記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）のいずれかで表される基であり、
　Ｌ１及びＬ２は、それぞれ独立に、
　　単結合、又は
　　置換もしくは無置換の環形成炭素数６～５０のアリーレン基であり、
　Ｙ１は、酸素原子又は硫黄原子であり、
　Ｒ２１～Ｒ２８のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　Ｒ１００並びに、前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８は、それぞれ独立に、
　　水素原子、
　　ハロゲン原子、
　　シアノ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、
　　置換もしくは無置換の炭素数１～３０のアルキル基、
　　置換もしくは無置換の炭素数１～３０のハロゲン化アルキル基、
　　置換もしくは無置換の環形成炭素数３～３０のシクロアルキル基、
　　置換もしくは無置換の炭素数２～３０のアルケニル基、
　　置換もしくは無置換の炭素数２～３０のアルキニル基、
　　置換もしくは無置換の炭素数３～３０のアルキルシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールホスホリル基、
　　ヒドロキシ基、
　　置換もしくは無置換の炭素数１～３０のアルコキシ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリールオキシ基、
　　－Ｎ（Ｒｚ）２で表される基、
　　チオール基、
　　置換もしくは無置換の炭素数１～３０のアルキルチオ基、
　　置換もしくは無置換の環形成炭素数７～３０のアラルキル基、
　　置換ゲルマニウム基、
　　置換ホスフィンオキシド基、
　　ニトロ基、
　　置換ボリル基、又は
　　置換もしくは無置換の環形成炭素数６～３０のアリールチオ基であり、
　Ｒｚは、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、又は
　　置換もしくは無置換の炭素数１～３０のアルキル基であり、
　－Ｎ（Ｒｚ）２における２つのＲｚは、互いに同一であるか、又は異なり、
　複数のＲ１００は、互いに同一であるか、又は異なり、
　前記一般式（１－１）及び（１－２）中、＊は、Ｒ２１～Ｒ２４が結合する六員環の炭素原子のいずれか１つとの結合位置を表す。） (In the general formulas (1-1) and (1-2),
A is a group represented by any of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
L 1 and L 2 are each independently,
A single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,
Y 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 21 to R 28 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 100 and R 21 to R 28 that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring are each independently,
hydrogen atom,
halogen atom,
cyano group,
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
Substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
Substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,
hydroxy group,
a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
-N(Rz) a group represented by 2 ,
thiol group,
a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms,
substituted germanium group,
substituted phosphine oxide group,
nitro group,
A substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
Rz is
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
-N(Rz) The two Rz in 2 are the same or different,
A plurality of R 100s are the same or different from each other,
In the general formulas (1-1) and (1-2), * represents the bonding position to any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded. )

（前記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）において、
　Ｘ１は、酸素原子又は硫黄原子であり、
　Ｒ１１～Ｒ２０のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ１１～Ｒ２０は、それぞれ独立に、前記一般式（１－１）及び（１－２）における前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８と同義であり、＊は、結合位置を表す。） (In the general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
X 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 11 to R 20 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 11 to R 20 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently represented by the general formulas (1-1) and (1-2). It has the same meaning as R 21 to R 28 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, and * represents a bonding position. )

　本発明の一態様によれば、前述の本発明の一態様に係る有機エレクトロルミネッセンス素子を搭載した電子機器が提供される。 According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescent element according to the above-described one aspect of the present invention.

　本発明の一態様によれば、下記一般式（１００－１）～（１００－４）のいずれかで表される化合物が提供される。 According to one aspect of the present invention, a compound represented by any of the following general formulas (100-1) to (100-4) is provided.

（前記一般式（１００－１）～（１００－４）において、
　Ａは、下記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）のいずれかで表される基であり、
　Ｌ１及びＬ２は、それぞれ独立に、
　　単結合、又は
　　置換もしくは無置換の環形成炭素数６～５０のアリーレン基であり、
　Ｙ１は、酸素原子又は硫黄原子であり、
　Ｒ２１～Ｒ２８のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　Ｒ１００並びに、前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８は、それぞれ独立に、
　　水素原子、
　　ハロゲン原子、
　　シアノ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、
　　置換もしくは無置換の炭素数１～３０のアルキル基、
　　置換もしくは無置換の炭素数１～３０のハロゲン化アルキル基、
　　置換もしくは無置換の環形成炭素数３～３０のシクロアルキル基、
　　置換もしくは無置換の炭素数２～３０のアルケニル基、
　　置換もしくは無置換の炭素数２～３０のアルキニル基、
　　置換もしくは無置換の炭素数３～３０のアルキルシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールホスホリル基、
　　ヒドロキシ基、
　　置換もしくは無置換の炭素数１～３０のアルコキシ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリールオキシ基、
　　－Ｎ（Ｒｚ）２で表される基、
　　チオール基、
　　置換もしくは無置換の炭素数１～３０のアルキルチオ基、
　　置換もしくは無置換の環形成炭素数７～３０のアラルキル基、
　　置換ゲルマニウム基、
　　置換ホスフィンオキシド基、
　　ニトロ基、
　　置換ボリル基、又は
　　置換もしくは無置換の環形成炭素数６～３０のアリールチオ基であり、
　Ｒｚは、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、又は
　　置換もしくは無置換の炭素数１～３０のアルキル基であり、
　－Ｎ（Ｒｚ）２における２つのＲｚは、互いに同一であるか、又は異なり、
　複数のＲ１００は、互いに同一であるか、又は異なり、
　ただし、前記一般式（１００－４）中、Ｒ１００は、－Ｎ（Ｒｚ）２で表される基ではない。
　前記一般式（１００－４）中、＊は、Ｒ２１～Ｒ２４が結合する六員環の炭素原子のいずれか１つとの結合位置を表す。） (In the general formulas (100-1) to (100-4),
A is a group represented by any of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
L 1 and L 2 are each independently,
A single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,
Y 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 21 to R 28 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 100 and R 21 to R 28 that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring are each independently,
hydrogen atom,
halogen atom,
cyano group,
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
Substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
Substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,
hydroxy group,
a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
-N(Rz) a group represented by 2 ,
thiol group,
a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms,
substituted germanium group,
substituted phosphine oxide group,
nitro group,
A substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
Rz is
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
-N(Rz) The two Rz in 2 are the same or different,
A plurality of R 100s are the same or different from each other,
However, in the general formula (100-4), R 100 is not a group represented by -N(Rz) 2 .
In the general formula (100-4), * represents the bonding position to any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded. )

（前記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）において、
　Ｘ１は、酸素原子又は硫黄原子であり、
　Ｒ１１～Ｒ２０のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ１１～Ｒ２０は、それぞれ独立に、前記一般式（１００－１）～（１００－４）における前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８と同義であり、＊は、結合位置を表す。） (In the general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
X 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 11 to R 20 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 11 to R 20 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently represented by the general formulas (100-1) to (100-4). It has the same meaning as R 21 to R 28 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, and * represents a bonding position. )

　本発明の一態様によれば、高性能な有機エレクトロルミネッセンス素子、高性能な有機エレクトロルミネッセンス素子を実現できる化合物、及び当該有機ＥＬ素子を搭載した電子機器を提供することができる。 According to one aspect of the present invention, it is possible to provide a high-performance organic electroluminescent device, a compound that can realize a high-performance organic electroluminescent device, and an electronic device equipped with the organic EL device.

本発明の第一実施形態に係る有機エレクトロルミネッセンス素子の一例の概略構成を示す図である。1 is a diagram showing a schematic configuration of an example of an organic electroluminescent device according to a first embodiment of the present invention. 過渡ＰＬを測定する装置の概略図である。FIG. 2 is a schematic diagram of an apparatus for measuring transient PL. 過渡ＰＬの減衰曲線の一例を示す図である。It is a figure which shows an example of the attenuation curve of transient PL. 本発明の第一実施形態に係る有機エレクトロルミネッセンス素子の一例の発光層における化合物Ｍ３及び化合物Ｍ２のエネルギー準位の関係を示す図である。FIG. 3 is a diagram showing the relationship between the energy levels of compound M3 and compound M2 in the light emitting layer of an example of the organic electroluminescent device according to the first embodiment of the present invention. 本発明の第二実施形態に係る有機エレクトロルミネッセンス素子の一例の発光層における化合物Ｍ３、化合物Ｍ２及び化合物Ｍ１のエネルギー準位、並びにエネルギー移動の関係を示す図である。It is a figure which shows the energy level of compound M3, compound M2, and compound M1 in the light emitting layer of an example of the organic electroluminescent element based on 2nd embodiment of this invention, and the relationship of energy transfer.

［定義］
　本明細書において、水素原子とは、中性子数が異なる同位体、即ち、軽水素（protium）、重水素（deuterium）、及び三重水素（tritium）を包含する。 [Definition]
In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, ie, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).

　本明細書において、化学構造式中、「Ｒ」等の記号や重水素原子を表す「Ｄ」が明示されていない結合可能位置には、水素原子、即ち、軽水素原子、重水素原子、又は三重水素原子が結合しているものとする。 In this specification, in a chemical structural formula, a hydrogen atom, that is, a light hydrogen atom, a deuterium atom, or Assume that tritium atoms are bonded.

　本明細書において、環形成炭素数とは、原子が環状に結合した構造の化合物（例えば、単環化合物、縮合環化合物、架橋化合物、炭素環化合物、及び複素環化合物）の当該環自体を構成する原子のうちの炭素原子の数を表す。当該環が置換基によって置換される場合、置換基に含まれる炭素は環形成炭素数には含まない。以下で記される「環形成炭素数」については、別途記載のない限り同様とする。例えば、ベンゼン環は環形成炭素数が６であり、ナフタレン環は環形成炭素数が１０であり、ピリジン環は環形成炭素数５であり、フラン環は環形成炭素数４である。また、例えば、９，９－ジフェニルフルオレニル基の環形成炭素数は１３であり、９，９’－スピロビフルオレニル基の環形成炭素数は２５である。
　また、ベンゼン環に置換基として、例えば、アルキル基が置換している場合、当該アルキル基の炭素数は、ベンゼン環の環形成炭素数に含めない。そのため、アルキル基が置換しているベンゼン環の環形成炭素数は、６である。また、ナフタレン環に置換基として、例えば、アルキル基が置換している場合、当該アルキル基の炭素数は、ナフタレン環の環形成炭素数に含めない。そのため、アルキル基が置換しているナフタレン環の環形成炭素数は、１０である。 In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). represents the number of carbon atoms among the atoms. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of carbon atoms forming the ring. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 carbon atoms, a naphthalene ring has 10 carbon atoms, a pyridine ring has 5 carbon atoms, and a furan ring has 4 carbon atoms. Further, for example, the number of ring carbon atoms in the 9,9-diphenylfluorenyl group is 13, and the number of ring carbon atoms in the 9,9'-spirobifluorenyl group is 25.
Further, when the benzene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the benzene ring. Therefore, the number of ring carbon atoms in the benzene ring substituted with an alkyl group is 6. Further, when the naphthalene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the naphthalene ring. Therefore, the number of ring carbon atoms in the naphthalene ring substituted with an alkyl group is 10.

　本明細書において、環形成原子数とは、原子が環状に結合した構造（例えば、単環、縮合環、及び環集合）の化合物（例えば、単環化合物、縮合環化合物、架橋化合物、炭素環化合物、及び複素環化合物）の当該環自体を構成する原子の数を表す。環を構成しない原子（例えば、環を構成する原子の結合を終端する水素原子）や、当該環が置換基によって置換される場合の置換基に含まれる原子は環形成原子数には含まない。以下で記される「環形成原子数」については、別途記載のない限り同様とする。例えば、ピリジン環の環形成原子数は６であり、キナゾリン環の環形成原子数は１０であり、フラン環の環形成原子数は５である。例えば、ピリジン環に結合している水素原子、又は置換基を構成する原子の数は、ピリジン環形成原子数の数に含めない。そのため、水素原子、又は置換基が結合しているピリジン環の環形成原子数は、６である。また、例えば、キナゾリン環の炭素原子に結合している水素原子、又は置換基を構成する原子については、キナゾリン環の環形成原子数の数に含めない。そのため、水素原子、又は置換基が結合しているキナゾリン環の環形成原子数は１０である。 In this specification, the number of ring-forming atoms refers to compounds with a structure in which atoms are bonded in a cyclic manner (e.g., monocyclic, fused ring, and ring assembly) (e.g., monocyclic compound, fused ring compound, bridged compound, carbocyclic compound). Represents the number of atoms that constitute the ring itself (compounds and heterocyclic compounds). Atoms that do not form a ring (for example, a hydrogen atom that terminates a bond between atoms that form a ring) and atoms that are included in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is the same unless otherwise specified. For example, the number of ring atoms in the pyridine ring is 6, the number of ring atoms in the quinazoline ring is 10, and the number of ring atoms in the furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents is not included in the number of atoms forming the pyridine ring. Therefore, the number of ring atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is six. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring atoms in the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

　本明細書において、「置換もしくは無置換の炭素数ＸＸ～ＹＹのＺＺ基」という表現における「炭素数ＸＸ～ＹＹ」は、ＺＺ基が無置換である場合の炭素数を表し、置換されている場合の置換基の炭素数を含めない。ここで、「ＹＹ」は、「ＸＸ」よりも大きく、「ＸＸ」は、１以上の整数を意味し、「ＹＹ」は、２以上の整数を意味する。 In the present specification, "carbon number XX to YY" in the expression "substituted or unsubstituted ZZ group with carbon number XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of carbon atoms in substituents. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

　本明細書において、「置換もしくは無置換の原子数ＸＸ～ＹＹのＺＺ基」という表現における「原子数ＸＸ～ＹＹ」は、ＺＺ基が無置換である場合の原子数を表し、置換されている場合の置換基の原子数を含めない。ここで、「ＹＹ」は、「ＸＸ」よりも大きく、「ＸＸ」は、１以上の整数を意味し、「ＹＹ」は、２以上の整数を意味する。 In this specification, "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group with number of atoms XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of atoms of substituents in case. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

　本明細書において、無置換のＺＺ基とは「置換もしくは無置換のＺＺ基」が「無置換のＺＺ基」である場合を表し、置換のＺＺ基とは「置換もしくは無置換のＺＺ基」が「置換のＺＺ基」である場合を表す。
　本明細書において、「置換もしくは無置換のＺＺ基」という場合における「無置換」とは、ＺＺ基における水素原子が置換基と置き換わっていないことを意味する。「無置換のＺＺ基」における水素原子は、軽水素原子、重水素原子、又は三重水素原子である。
　また、本明細書において、「置換もしくは無置換のＺＺ基」という場合における「置換」とは、ＺＺ基における１つ以上の水素原子が、置換基と置き換わっていることを意味する。「ＡＡ基で置換されたＢＢ基」という場合における「置換」も同様に、ＢＢ基における１つ以上の水素原子が、ＡＡ基と置き換わっていることを意味する。 In this specification, an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a "substituted or unsubstituted ZZ group". represents the case where is a "substituted ZZ group".
In the present specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a light hydrogen atom, a deuterium atom, or a tritium atom.
Furthermore, in this specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. "Substitution" in the case of "BB group substituted with an AA group" similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.

「本明細書に記載の置換基」
　以下、本明細書に記載の置換基について説明する。 "Substituents described herein"
The substituents described in this specification will be explained below.

　本明細書に記載の「無置換のアリール基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
　本明細書に記載の「無置換の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
　本明細書に記載の「無置換のアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。
　本明細書に記載の「無置換のアルケニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
　本明細書に記載の「無置換のアルキニル基」の炭素数は、本明細書に別途記載のない限り、２～５０であり、好ましくは２～２０、より好ましくは２～６である。
　本明細書に記載の「無置換のシクロアルキル基」の環形成炭素数は、本明細書に別途記載のない限り、３～５０であり、好ましくは３～２０、より好ましくは３～６である。
　本明細書に記載の「無置換のアリーレン基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０、より好ましくは６～１８である。
　本明細書に記載の「無置換の２価の複素環基」の環形成原子数は、本明細書に別途記載のない限り、５～５０であり、好ましくは５～３０、より好ましくは５～１８である。
　本明細書に記載の「無置換のアルキレン基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０、より好ましくは１～６である。 The number of ring carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified herein. .
The number of ring atoms of the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified herein. be.
The number of carbon atoms in the "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.
The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified herein.
Unless otherwise specified herein, the number of ring carbon atoms in the "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6. be.
Unless otherwise specified herein, the number of ring carbon atoms in the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18. .
The number of ring atoms of the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, more preferably 5 unless otherwise specified herein. ~18.
The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified herein.

・「置換もしくは無置換のアリール基」
　本明細書に記載の「置換もしくは無置換のアリール基」の具体例（具体例群Ｇ１）としては、以下の無置換のアリール基（具体例群Ｇ１Ａ）及び置換のアリール基（具体例群Ｇ１Ｂ）等が挙げられる。（ここで、無置換のアリール基とは「置換もしくは無置換のアリール基」が「無置換のアリール基」である場合を指し、置換のアリール基とは「置換もしくは無置換のアリール基」が「置換のアリール基」である場合を指す。）本明細書において、単に「アリール基」という場合は、「無置換のアリール基」と「置換のアリール基」の両方を含む。
　「置換のアリール基」は、「無置換のアリール基」の１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアリール基」としては、例えば、下記具体例群Ｇ１Ａの「無置換のアリール基」の１つ以上の水素原子が置換基と置き換わった基、及び下記具体例群Ｇ１Ｂの置換のアリール基の例等が挙げられる。尚、ここに列挙した「無置換のアリール基」の例、及び「置換のアリール基」の例は、一例に過ぎず、本明細書に記載の「置換のアリール基」には、下記具体例群Ｇ１Ｂの「置換のアリール基」におけるアリール基自体の炭素原子に結合する水素原子がさらに置換基と置き換わった基、及び下記具体例群Ｇ１Ｂの「置換のアリール基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・“Substituted or unsubstituted aryl group”
Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B). ) etc. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is (Refers to the case where it is a "substituted aryl group.") In this specification, the mere mention of "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group."
"Substituted aryl group" means a group in which one or more hydrogen atoms of "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of the "unsubstituted aryl group" in the specific example group G1A below are replaced with a substituent, and a substituted aryl group in the following specific example group G1B. Examples include: The examples of "unsubstituted aryl group" and "substituted aryl group" listed here are just examples, and the "substituted aryl group" described in this specification includes the following specific examples. A group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of Group G1B is further replaced with a substituent, and a hydrogen atom of the substituent in the "substituted aryl group" in the following specific example group G1B is Furthermore, groups substituted with substituents are also included.

・無置換のアリール基（具体例群Ｇ１Ａ）：
フェニル基、
ｐ－ビフェニル基、
ｍ－ビフェニル基、
ｏ－ビフェニル基、
ｐ－ターフェニル－４－イル基、
ｐ－ターフェニル－３－イル基、
ｐ－ターフェニル－２－イル基、
ｍ－ターフェニル－４－イル基、
ｍ－ターフェニル－３－イル基、
ｍ－ターフェニル－２－イル基、
ｏ－ターフェニル－４－イル基、
ｏ－ターフェニル－３－イル基、
ｏ－ターフェニル－２－イル基、
１－ナフチル基、
２－ナフチル基、
アントリル基、
ベンゾアントリル基、
フェナントリル基、
ベンゾフェナントリル基、
フェナレニル基、
ピレニル基、
クリセニル基、
ベンゾクリセニル基、
トリフェニレニル基、
ベンゾトリフェニレニル基、
テトラセニル基、
ペンタセニル基、
フルオレニル基、
９，９’－スピロビフルオレニル基、
ベンゾフルオレニル基、
ジベンゾフルオレニル基、
フルオランテニル基、
ベンゾフルオランテニル基、
ペリレニル基、及び
下記一般式（ＴＥＭＰ－１）～（ＴＥＭＰ－１５）で表される環構造から１つの水素原子を除くことにより誘導される１価のアリール基。 ・Unsubstituted aryl group (specific example group G1A):
phenyl group,
p-biphenyl group,
m-biphenyl group,
o-biphenyl group,
p-terphenyl-4-yl group,
p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
anthryl group,
benzanthryl group,
phenanthryl group,
benzophenanthryl group,
phenalenyl group,
pyrenyl group,
chrysenyl group,
benzocrysenyl group,
triphenylenyl group,
benzotriphenylenyl group,
tetracenyl group,
pentacenyl group,
fluorenyl group,
9,9'-spirobifluorenyl group,
benzofluorenyl group,
dibenzofluorenyl group,
fluoranthenyl group,
benzofluoranthenyl group,
A monovalent aryl group derived by removing one hydrogen atom from a perylenyl group and a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

・置換のアリール基（具体例群Ｇ１Ｂ）：
ｏ－トリル基、
ｍ－トリル基、
ｐ－トリル基、
パラ－キシリル基、
メタ－キシリル基、
オルト－キシリル基、
パラ－イソプロピルフェニル基、
メタ－イソプロピルフェニル基、
オルト－イソプロピルフェニル基、
パラ－ｔ－ブチルフェニル基、
メタ－ｔ－ブチルフェニル基、
オルト－ｔ－ブチルフェニル基、
３，４，５－トリメチルフェニル基、
９，９－ジメチルフルオレニル基、
９，９－ジフェニルフルオレニル基、
９，９－ビス（４－メチルフェニル）フルオレニル基、
９，９－ビス（４－イソプロピルフェニル）フルオレニル基、
９，９－ビス（４－ｔ－ブチルフェニル）フルオレニル基、
シアノフェニル基、
トリフェニルシリルフェニル基、
トリメチルシリルフェニル基、
フェニルナフチル基、
ナフチルフェニル基、及び
前記一般式（ＴＥＭＰ－１）～（ＴＥＭＰ－１５）で表される環構造から誘導される１価の基の１つ以上の水素原子が置換基と置き換わった基。 ・Substituted aryl group (specific example group G1B):
o-tolyl group,
m-tolyl group,
p-tolyl group,
para-xylyl group,
meta-xylyl group,
ortho-xylyl group,
para-isopropylphenyl group,
meta-isopropylphenyl group,
ortho-isopropylphenyl group,
para-t-butylphenyl group,
meta-t-butylphenyl group,
ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-dimethylfluorenyl group,
9,9-diphenylfluorenyl group,
9,9-bis(4-methylphenyl)fluorenyl group,
9,9-bis(4-isopropylphenyl)fluorenyl group,
9,9-bis(4-t-butylphenyl)fluorenyl group,
cyanophenyl group,
triphenylsilylphenyl group,
trimethylsilylphenyl group,
phenylnaphthyl group,
A group in which one or more hydrogen atoms of a monovalent group derived from a naphthylphenyl group and a ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are replaced with a substituent.

・「置換もしくは無置換の複素環基」
　本明細書に記載の「複素環基」は、環形成原子にヘテロ原子を少なくとも１つ含む環状の基である。ヘテロ原子の具体例としては、窒素原子、酸素原子、硫黄原子、ケイ素原子、リン原子、及びホウ素原子が挙げられる。
　本明細書に記載の「複素環基」は、単環の基であるか、又は縮合環の基である。
　本明細書に記載の「複素環基」は、芳香族複素環基であるか、又は非芳香族複素環基である。
　本明細書に記載の「置換もしくは無置換の複素環基」の具体例（具体例群Ｇ２）としては、以下の無置換の複素環基（具体例群Ｇ２Ａ）、及び置換の複素環基（具体例群Ｇ２Ｂ）等が挙げられる。（ここで、無置換の複素環基とは「置換もしくは無置換の複素環基」が「無置換の複素環基」である場合を指し、置換の複素環基とは「置換もしくは無置換の複素環基」が「置換の複素環基」である場合を指す。）本明細書において、単に「複素環基」という場合は、「無置換の複素環基」と「置換の複素環基」の両方を含む。
　「置換の複素環基」は、「無置換の複素環基」の１つ以上の水素原子が置換基と置き換わった基を意味する。「置換の複素環基」の具体例は、下記具体例群Ｇ２Ａの「無置換の複素環基」の水素原子が置き換わった基、及び下記具体例群Ｇ２Ｂの置換の複素環基の例等が挙げられる。尚、ここに列挙した「無置換の複素環基」の例や「置換の複素環基」の例は、一例に過ぎず、本明細書に記載の「置換の複素環基」には、具体例群Ｇ２Ｂの「置換の複素環基」における複素環基自体の環形成原子に結合する水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ２Ｂの「置換の複素環基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・“Substituted or unsubstituted heterocyclic group”
The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of heteroatoms include nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom.
A "heterocyclic group" as described herein is a monocyclic group or a fused ring group.
A "heterocyclic group" as described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
Specific examples of the "substituted or unsubstituted heterocyclic group" (specific example group G2) described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group ( Examples include specific example group G2B). (Here, the term "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and the term "substituted heterocyclic group" refers to "substituted or unsubstituted heterocyclic group"). "Heterocyclic group" refers to a "substituted heterocyclic group.") In this specification, simply "heterocyclic group" refers to "unsubstituted heterocyclic group" and "substituted heterocyclic group." including both.
"Substituted heterocyclic group" means a group in which one or more hydrogen atoms of "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include a group in which the hydrogen atom of the "unsubstituted heterocyclic group" in specific example group G2A is replaced, and examples of substituted heterocyclic groups in specific example group G2B below. Can be mentioned. The examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are just examples, and the "substituted heterocyclic group" described in this specification includes specific A group in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" in example group G2B is further replaced with a substituent, and a substituent in the "substituted heterocyclic group" in specific example group G2B Also included are groups in which a hydrogen atom is further replaced with a substituent.

　具体例群Ｇ２Ａは、例えば、以下の窒素原子を含む無置換の複素環基（具体例群Ｇ２Ａ１）、酸素原子を含む無置換の複素環基（具体例群Ｇ２Ａ２）、硫黄原子を含む無置換の複素環基（具体例群Ｇ２Ａ３）、及び下記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から１つの水素原子を除くことにより誘導される１価の複素環基（具体例群Ｇ２Ａ４）を含む。 Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), and unsubstituted heterocyclic groups containing a sulfur atom. heterocyclic group (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific example group G2A4).

　具体例群Ｇ２Ｂは、例えば、以下の窒素原子を含む置換の複素環基（具体例群Ｇ２Ｂ１）、酸素原子を含む置換の複素環基（具体例群Ｇ２Ｂ２）、硫黄原子を含む置換の複素環基（具体例群Ｇ２Ｂ３）、及び下記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基の１つ以上の水素原子が置換基と置き換わった基（具体例群Ｇ２Ｂ４）を含む。 Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), and substituted heterocyclic groups containing a sulfur atom. group (Specific Example Group G2B3), and one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are substituents. Includes substituted groups (Example Group G2B4).

・窒素原子を含む無置換の複素環基（具体例群Ｇ２Ａ１）：
ピロリル基、
イミダゾリル基、
ピラゾリル基、
トリアゾリル基、
テトラゾリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ピリジル基、
ピリダジニル基、
ピリミジニル基、
ピラジニル基、
トリアジニル基、
インドリル基、
イソインドリル基、
インドリジニル基、
キノリジニル基、
キノリル基、
イソキノリル基、
シンノリル基、
フタラジニル基、
キナゾリニル基、
キノキサリニル基、
ベンゾイミダゾリル基、
インダゾリル基、
フェナントロリニル基、
フェナントリジニル基、
アクリジニル基、
フェナジニル基、
カルバゾリル基、
ベンゾカルバゾリル基、
モルホリノ基、
フェノキサジニル基、
フェノチアジニル基、
アザカルバゾリル基、及び
ジアザカルバゾリル基。 ・Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):
pyrrolyl group,
imidazolyl group,
pyrazolyl group,
triazolyl group,
Tetrazolyl group,
oxazolyl group,
isoxazolyl group,
oxadiazolyl group,
thiazolyl group,
isothiazolyl group,
thiadiazolyl group,
pyridyl group,
pyridazinyl group,
pyrimidinyl group,
pyrazinyl group,
triazinyl group,
indolyl group,
isoindolyl group,
indolizinyl group,
quinolidinyl group,
quinolyl group,
isoquinolyl group,
cinnolyl group,
phthalazinyl group,
quinazolinyl group,
quinoxalinyl group,
benzimidazolyl group,
indazolyl group,
phenanthrolinyl group,
phenanthridinyl group,
acridinyl group,
phenazinyl group,
carbazolyl group,
benzocarbazolyl group,
morpholino group,
phenoxazinyl group,
phenothiazinyl group,
Azacarbazolyl group and diazacarbazolyl group.

・酸素原子を含む無置換の複素環基（具体例群Ｇ２Ａ２）：
フリル基、
オキサゾリル基、
イソオキサゾリル基、
オキサジアゾリル基、
キサンテニル基、
ベンゾフラニル基、
イソベンゾフラニル基、
ジベンゾフラニル基、
ナフトベンゾフラニル基、
ベンゾオキサゾリル基、
ベンゾイソキサゾリル基、
フェノキサジニル基、
モルホリノ基、
ジナフトフラニル基、
アザジベンゾフラニル基、
ジアザジベンゾフラニル基、
アザナフトベンゾフラニル基、及び
ジアザナフトベンゾフラニル基。 ・Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):
frill group,
oxazolyl group,
isoxazolyl group,
oxadiazolyl group,
xanthenyl group,
benzofuranyl group,
isobenzofuranyl group,
dibenzofuranyl group,
naphthobenzofuranyl group,
benzoxazolyl group,
benzisoxazolyl group,
phenoxazinyl group,
morpholino group,
dinaphthofuranyl group,
azadibenzofuranyl group,
diazadibenzofuranyl group,
Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.

・硫黄原子を含む無置換の複素環基（具体例群Ｇ２Ａ３）：
チエニル基、
チアゾリル基、
イソチアゾリル基、
チアジアゾリル基、
ベンゾチオフェニル基（ベンゾチエニル基）、
イソベンゾチオフェニル基（イソベンゾチエニル基）、
ジベンゾチオフェニル基（ジベンゾチエニル基）、
ナフトベンゾチオフェニル基（ナフトベンゾチエニル基）、
ベンゾチアゾリル基、
ベンゾイソチアゾリル基、
フェノチアジニル基、
ジナフトチオフェニル基（ジナフトチエニル基）、
アザジベンゾチオフェニル基（アザジベンゾチエニル基）、
ジアザジベンゾチオフェニル基（ジアザジベンゾチエニル基）、
アザナフトベンゾチオフェニル基（アザナフトベンゾチエニル基）、及び
ジアザナフトベンゾチオフェニル基（ジアザナフトベンゾチエニル基）。 ・Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):
thienyl group,
thiazolyl group,
isothiazolyl group,
thiadiazolyl group,
benzothiophenyl group (benzothienyl group),
Isobenzothiophenyl group (isobenzothienyl group),
dibenzothiophenyl group (dibenzothienyl group),
naphthobenzothiophenyl group (naphthobenzothienyl group),
benzothiazolyl group,
benzisothiazolyl group,
phenothiazinyl group,
dinaphthothiophenyl group (dinaphthothienyl group),
Azadibenzothiophenyl group (azadibenzothienyl group),
Diazadibenzothiophenyl group (diazadibenzothienyl group),
Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

・下記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から１つの水素原子を除くことにより誘導される１価の複素環基（具体例群Ｇ２Ａ４）： - Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

　前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）において、ＸＡ及びＹＡは、それぞれ独立に、酸素原子、硫黄原子、ＮＨ、又はＣＨ２である。ただし、ＸＡ及びＹＡのうち少なくとも１つは、酸素原子、硫黄原子、又はＮＨである。
　前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）において、ＸＡ及びＹＡの少なくともいずれかがＮＨ、又はＣＨ２である場合、前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基には、これらＮＨ、又はＣＨ２から１つの水素原子を除いて得られる１価の基が含まれる。 In the general formulas (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH 2 . However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.
In the general formulas (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH or CH 2 , in the general formulas (TEMP-16) to (TEMP-33), The monovalent heterocyclic group derived from the represented ring structure includes a monovalent group obtained by removing one hydrogen atom from these NH or CH 2 .

・窒素原子を含む置換の複素環基（具体例群Ｇ２Ｂ１）：
（９－フェニル）カルバゾリル基、
（９－ビフェニリル）カルバゾリル基、
（９－フェニル）フェニルカルバゾリル基、
（９－ナフチル）カルバゾリル基、
ジフェニルカルバゾール－９－イル基、
フェニルカルバゾール－９－イル基、
メチルベンゾイミダゾリル基、
エチルベンゾイミダゾリル基、
フェニルトリアジニル基、
ビフェニリルトリアジニル基、
ジフェニルトリアジニル基、
フェニルキナゾリニル基、及びビフェニリルキナゾリニル基。 ・Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):
(9-phenyl)carbazolyl group,
(9-biphenylyl)carbazolyl group,
(9-phenyl)phenylcarbazolyl group,
(9-naphthyl)carbazolyl group,
diphenylcarbazol-9-yl group,
phenylcarbazol-9-yl group,
methylbenzimidazolyl group,
ethylbenzimidazolyl group,
phenyltriazinyl group,
biphenylyltriazinyl group,
diphenyltriazinyl group,
phenylquinazolinyl group, and biphenylylquinazolinyl group.

・酸素原子を含む置換の複素環基（具体例群Ｇ２Ｂ２）：
フェニルジベンゾフラニル基、
メチルジベンゾフラニル基、
ｔ－ブチルジベンゾフラニル基、及び
スピロ［９Ｈ－キサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基。 ・Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):
phenyldibenzofuranyl group,
methyldibenzofuranyl group,
A t-butyldibenzofuranyl group and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

・硫黄原子を含む置換の複素環基（具体例群Ｇ２Ｂ３）：
フェニルジベンゾチオフェニル基、
メチルジベンゾチオフェニル基、
ｔ－ブチルジベンゾチオフェニル基、及び
スピロ［９Ｈ－チオキサンテン－９，９’－［９Ｈ］フルオレン］の１価の残基。 ・Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):
phenyldibenzothiophenyl group,
methyldibenzothiophenyl group,
A t-butyldibenzothiophenyl group and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

・前記一般式（ＴＥＭＰ－１６）～（ＴＥＭＰ－３３）で表される環構造から誘導される１価の複素環基の１つ以上の水素原子が置換基と置き換わった基（具体例群Ｇ２Ｂ４）： - A group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) is replaced with a substituent (specific example group G2B4) ):

　前記「１価の複素環基の１つ以上の水素原子」とは、該１価の複素環基の環形成炭素原子に結合している水素原子、ＸＡ及びＹＡの少なくともいずれかがＮＨである場合の窒素原子に結合している水素原子、及びＸＡ及びＹＡの一方がＣＨ２である場合のメチレン基の水素原子から選ばれる１つ以上の水素原子を意味する。 The above-mentioned "one or more hydrogen atoms of a monovalent heterocyclic group" means a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, at least one of X A and Y A is NH It means one or more hydrogen atoms selected from a hydrogen atom bonded to a nitrogen atom when the above is the case, and a hydrogen atom of a methylene group when one of X A and Y A is CH 2 .

・「置換もしくは無置換のアルキル基」
　本明細書に記載の「置換もしくは無置換のアルキル基」の具体例（具体例群Ｇ３）としては、以下の無置換のアルキル基（具体例群Ｇ３Ａ）及び置換のアルキル基（具体例群Ｇ３Ｂ）が挙げられる。（ここで、無置換のアルキル基とは「置換もしくは無置換のアルキル基」が「無置換のアルキル基」である場合を指し、置換のアルキル基とは「置換もしくは無置換のアルキル基」が「置換のアルキル基」である場合を指す。）以下、単に「アルキル基」という場合は、「無置換のアルキル基」と「置換のアルキル基」の両方を含む。
　「置換のアルキル基」は、「無置換のアルキル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルキル基」の具体例としては、下記の「無置換のアルキル基」（具体例群Ｇ３Ａ）における１つ以上の水素原子が置換基と置き換わった基、及び置換のアルキル基（具体例群Ｇ３Ｂ）の例等が挙げられる。本明細書において、「無置換のアルキル基」におけるアルキル基は、鎖状のアルキル基を意味する。そのため、「無置換のアルキル基」は、直鎖である「無置換のアルキル基」、及び分岐状である「無置換のアルキル基」が含まれる。尚、ここに列挙した「無置換のアルキル基」の例や「置換のアルキル基」の例は、一例に過ぎず、本明細書に記載の「置換のアルキル基」には、具体例群Ｇ３Ｂの「置換のアルキル基」におけるアルキル基自体の水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ３Ｂの「置換のアルキル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・“Substituted or unsubstituted alkyl group”
Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). ). (Here, an unsubstituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and a substituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group" is (This refers to the case where it is a "substituted alkyl group.") Hereinafter, when it is simply referred to as an "alkyl group," it includes both an "unsubstituted alkyl group" and a "substituted alkyl group."
"Substituted alkyl group" means a group in which one or more hydrogen atoms in "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include groups in which one or more hydrogen atoms in the "unsubstituted alkyl group" (specific example group G3A) below are replaced with a substituent, and substituted alkyl groups (specific examples Examples include group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". The examples of "unsubstituted alkyl group" and "substituted alkyl group" listed here are just examples, and the "substituted alkyl group" described in this specification includes specific example group G3B. A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" in "Substituted alkyl group" is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group" in Example Group G3B is further replaced with a substituent. included.

・無置換のアルキル基（具体例群Ｇ３Ａ）：
メチル基、
エチル基、
ｎ－プロピル基、
イソプロピル基、
ｎ－ブチル基、
イソブチル基、
ｓ－ブチル基、及び
ｔ－ブチル基。 ・Unsubstituted alkyl group (specific example group G3A):
methyl group,
ethyl group,
n-propyl group,
isopropyl group,
n-butyl group,
isobutyl group,
s-butyl group and t-butyl group.

・置換のアルキル基（具体例群Ｇ３Ｂ）：
ヘプタフルオロプロピル基（異性体を含む）、
ペンタフルオロエチル基、
２，２，２－トリフルオロエチル基、及び
トリフルオロメチル基。 ・Substituted alkyl group (specific example group G3B):
heptafluoropropyl group (including isomers),
pentafluoroethyl group,
2,2,2-trifluoroethyl group and trifluoromethyl group.

・「置換もしくは無置換のアルケニル基」
　本明細書に記載の「置換もしくは無置換のアルケニル基」の具体例（具体例群Ｇ４）としては、以下の無置換のアルケニル基（具体例群Ｇ４Ａ）、及び置換のアルケニル基（具体例群Ｇ４Ｂ）等が挙げられる。（ここで、無置換のアルケニル基とは「置換もしくは無置換のアルケニル基」が「無置換のアルケニル基」である場合を指し、「置換のアルケニル基」とは「置換もしくは無置換のアルケニル基」が「置換のアルケニル基」である場合を指す。）本明細書において、単に「アルケニル基」という場合は、「無置換のアルケニル基」と「置換のアルケニル基」の両方を含む。
　「置換のアルケニル基」は、「無置換のアルケニル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルケニル基」の具体例としては、下記の「無置換のアルケニル基」（具体例群Ｇ４Ａ）が置換基を有する基、及び置換のアルケニル基（具体例群Ｇ４Ｂ）の例等が挙げられる。尚、ここに列挙した「無置換のアルケニル基」の例や「置換のアルケニル基」の例は、一例に過ぎず、本明細書に記載の「置換のアルケニル基」には、具体例群Ｇ４Ｂの「置換のアルケニル基」におけるアルケニル基自体の水素原子がさらに置換基と置き換わった基、及び具体例群Ｇ４Ｂの「置換のアルケニル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・“Substituted or unsubstituted alkenyl group”
Specific examples of the "substituted or unsubstituted alkenyl group" (specific example group G4) described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, the term "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to "substituted or unsubstituted alkenyl group"). " refers to the case where it is a "substituted alkenyl group.") In the present specification, simply "alkenyl group" includes both "unsubstituted alkenyl group" and "substituted alkenyl group."
"Substituted alkenyl group" means a group in which one or more hydrogen atoms in "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and the substituted alkenyl group (specific example group G4B). It will be done. The examples of "unsubstituted alkenyl group" and "substituted alkenyl group" listed here are just examples, and the "substituted alkenyl group" described in this specification includes specific example group G4B. A group in which the hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkenyl group" in Example Group G4B is further replaced with a substituent. included.

・無置換のアルケニル基（具体例群Ｇ４Ａ）：
ビニル基、
アリル基、
１－ブテニル基、
２－ブテニル基、及び
３－ブテニル基。 ・Unsubstituted alkenyl group (specific example group G4A):
vinyl group,
allyl group,
1-butenyl group,
2-butenyl group and 3-butenyl group.

・置換のアルケニル基（具体例群Ｇ４Ｂ）：
１，３－ブタンジエニル基、
１－メチルビニル基、
１－メチルアリル基、
１，１－ジメチルアリル基、
２－メチルアリル基、及び
１，２－ジメチルアリル基。 ・Substituted alkenyl group (specific example group G4B):
1,3-butandienyl group,
1-methylvinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-methylallyl group and 1,2-dimethylallyl group.

・「置換もしくは無置換のアルキニル基」
　本明細書に記載の「置換もしくは無置換のアルキニル基」の具体例（具体例群Ｇ５）としては、以下の無置換のアルキニル基（具体例群Ｇ５Ａ）等が挙げられる。（ここで、無置換のアルキニル基とは、「置換もしくは無置換のアルキニル基」が「無置換のアルキニル基」である場合を指す。）以下、単に「アルキニル基」という場合は、「無置換のアルキニル基」と「置換のアルキニル基」の両方を含む。
　「置換のアルキニル基」は、「無置換のアルキニル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のアルキニル基」の具体例としては、下記の「無置換のアルキニル基」（具体例群Ｇ５Ａ）における１つ以上の水素原子が置換基と置き換わった基等が挙げられる。 ・“Substituted or unsubstituted alkynyl group”
Specific examples of the "substituted or unsubstituted alkynyl group" (specific example group G5) described in this specification include the following unsubstituted alkynyl group (specific example group G5A). (Here, the term "unsubstituted alkynyl group" refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group.") Hereinafter, when simply "alkynyl group" is used, "unsubstituted alkynyl group" is referred to as "unsubstituted alkynyl group." ``alkynyl group'' and ``substituted alkynyl group.''
"Substituted alkynyl group" means a group in which one or more hydrogen atoms in "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with a substituent.

・無置換のアルキニル基（具体例群Ｇ５Ａ）：エチニル基。 - Unsubstituted alkynyl group (specific example group G5A): ethynyl group.

・「置換もしくは無置換のシクロアルキル基」
　本明細書に記載の「置換もしくは無置換のシクロアルキル基」の具体例（具体例群Ｇ６）としては、以下の無置換のシクロアルキル基（具体例群Ｇ６Ａ）、及び置換のシクロアルキル基（具体例群Ｇ６Ｂ）等が挙げられる。（ここで、無置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「無置換のシクロアルキル基」である場合を指し、置換のシクロアルキル基とは「置換もしくは無置換のシクロアルキル基」が「置換のシクロアルキル基」である場合を指す。）本明細書において、単に「シクロアルキル基」という場合は、「無置換のシクロアルキル基」と「置換のシクロアルキル基」の両方を含む。
　「置換のシクロアルキル基」は、「無置換のシクロアルキル基」における１つ以上の水素原子が置換基と置き換わった基を意味する。「置換のシクロアルキル基」の具体例としては、下記の「無置換のシクロアルキル基」（具体例群Ｇ６Ａ）における１つ以上の水素原子が置換基と置き換わった基、及び置換のシクロアルキル基（具体例群Ｇ６Ｂ）の例等が挙げられる。尚、ここに列挙した「無置換のシクロアルキル基」の例や「置換のシクロアルキル基」の例は、一例に過ぎず、本明細書に記載の「置換のシクロアルキル基」には、具体例群Ｇ６Ｂの「置換のシクロアルキル基」におけるシクロアルキル基自体の炭素原子に結合する１つ以上の水素原子が置換基と置き換わった基、及び具体例群Ｇ６Ｂの「置換のシクロアルキル基」における置換基の水素原子がさらに置換基と置き換わった基も含まれる。 ・“Substituted or unsubstituted cycloalkyl group”
Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups ( Examples include specific example group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group", and the term "substituted cycloalkyl group" refers to "substituted or unsubstituted cycloalkyl group"). ("cycloalkyl group" refers to the case where "substituted cycloalkyl group" is used.) In this specification, when simply referring to "cycloalkyl group", it refers to "unsubstituted cycloalkyl group" and "substituted cycloalkyl group". including both.
"Substituted cycloalkyl group" means a group in which one or more hydrogen atoms in "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and a substituted cycloalkyl group. (Specific example group G6B) and the like can be mentioned. The examples of "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" listed here are just examples, and the "substituted cycloalkyl group" described in this specification includes specific A group in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself is replaced with a substituent in the "substituted cycloalkyl group" of example group G6B, and in the "substituted cycloalkyl group" of specific example group G6B Also included are groups in which the hydrogen atom of a substituent is further replaced with a substituent.

・無置換のシクロアルキル基（具体例群Ｇ６Ａ）：
シクロプロピル基、
シクロブチル基、
シクロペンチル基、
シクロヘキシル基、
１－アダマンチル基、
２－アダマンチル基、
１－ノルボルニル基、及び
２－ノルボルニル基。 ・Unsubstituted cycloalkyl group (specific example group G6A):
cyclopropyl group,
cyclobutyl group,
cyclopentyl group,
cyclohexyl group,
1-adamantyl group,
2-adamantyl group,
1-norbornyl group and 2-norbornyl group.

・置換のシクロアルキル基（具体例群Ｇ６Ｂ）：
４－メチルシクロヘキシル基。 ・Substituted cycloalkyl group (specific example group G6B):
4-methylcyclohexyl group.

・「－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）で表される基」
　本明細書に記載の－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）で表される基の具体例（具体例群Ｇ７）としては、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ１）、
－Ｓｉ（Ｇ１）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ２）、
－Ｓｉ（Ｇ２）（Ｇ２）（Ｇ２）、
－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）、及び
－Ｓｉ（Ｇ６）（Ｇ６）（Ｇ６）
が挙げられる。ここで、
　Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
　Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
　Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
　Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。
　－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ１）における複数のＧ１は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ１）（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ１）（Ｇ１）（Ｇ２）における複数のＧ１は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ２）（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。
　－Ｓｉ（Ｇ６）（Ｇ６）（Ｇ６）における複数のＧ６は、互いに同一であるか、又は異なる。 ・"Group represented by -Si(R 901 )(R 902 )(R 903 )"
Specific examples of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification (specific example group G7) include:
-Si(G1)(G1)(G1),
-Si (G1) (G2) (G2),
-Si (G1) (G1) (G2),
-Si(G2)(G2)(G2),
-Si(G3)(G3)(G3), and -Si(G6)(G6)(G6)
can be mentioned. here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
- A plurality of G1's in Si(G1) (G1) (G1) are the same or different from each other.
- A plurality of G2's in Si(G1)(G2)(G2) are mutually the same or different.
- A plurality of G1's in Si(G1) (G1) (G2) are mutually the same or different.
- A plurality of G2's in Si(G2) (G2) (G2) are mutually the same or different.
- A plurality of G3's in Si(G3) (G3) (G3) are mutually the same or different.
- A plurality of G6's in Si(G6) (G6) (G6) are mutually the same or different.

・「－Ｏ－（Ｒ９０４）で表される基」
　本明細書に記載の－Ｏ－（Ｒ９０４）で表される基の具体例（具体例群Ｇ８）としては、
－Ｏ（Ｇ１）、
－Ｏ（Ｇ２）、
－Ｏ（Ｇ３）、及び
－Ｏ（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
　Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
　Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
　Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。 ・"Group represented by -O-(R 904 )"
Specific examples of the group represented by -O-(R 904 ) described in this specification (specific example group G8) include:
-O(G1),
-O(G2),
-O (G3) and -O (G6)
can be mentioned.
here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

・「－Ｓ－（Ｒ９０５）で表される基」
　本明細書に記載の－Ｓ－（Ｒ９０５）で表される基の具体例（具体例群Ｇ９）としては、
－Ｓ（Ｇ１）、
－Ｓ（Ｇ２）、
－Ｓ（Ｇ３）、及び
－Ｓ（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
　Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
　Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
　Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。 ・"Group represented by -S-(R 905 )"
Specific examples of the group represented by -S-(R 905 ) described in this specification (specific example group G9) include:
-S (G1),
-S (G2),
-S (G3) and -S (G6)
can be mentioned.
here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

・「－Ｎ（Ｒ９０６）（Ｒ９０７）で表される基」
　本明細書に記載の－Ｎ（Ｒ９０６）（Ｒ９０７）で表される基の具体例（具体例群Ｇ１０）としては、
－Ｎ（Ｇ１）（Ｇ１）、
－Ｎ（Ｇ２）（Ｇ２）、
－Ｎ（Ｇ１）（Ｇ２）、
－Ｎ（Ｇ３）（Ｇ３）、及び
－Ｎ（Ｇ６）（Ｇ６）
が挙げられる。
　ここで、
　Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。
　Ｇ２は、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」である。
　Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。
　Ｇ６は、具体例群Ｇ６に記載の「置換もしくは無置換のシクロアルキル基」である。
　－Ｎ（Ｇ１）（Ｇ１）における複数のＧ１は、互いに同一であるか、又は異なる。
　－Ｎ（Ｇ２）（Ｇ２）における複数のＧ２は、互いに同一であるか、又は異なる。
　－Ｎ（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。
　－Ｎ（Ｇ６）（Ｇ６）における複数のＧ６は、互いに同一であるか、又は異なる。 ・"Group represented by -N(R 906 )(R 907 )"
Specific examples of the group represented by -N(R 906 )(R 907 ) described in this specification (specific example group G10) include:
-N(G1)(G1),
-N(G2)(G2),
-N (G1) (G2),
-N (G3) (G3), and -N (G6) (G6)
can be mentioned.
here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
-N(G1) A plurality of G1's in (G1) are mutually the same or different.
-N(G2) A plurality of G2's in (G2) are the same or different.
-N(G3) A plurality of G3's in (G3) are mutually the same or different.
-N(G6) A plurality of G6's in (G6) are mutually the same or different.

・「ハロゲン原子」
　本明細書に記載の「ハロゲン原子」の具体例（具体例群Ｇ１１）としては、フッ素原子、塩素原子、臭素原子、及びヨウ素原子等が挙げられる。 ・"Halogen atom"
Specific examples of the "halogen atom" (specific example group G11) described in this specification include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.

・「置換もしくは無置換のフルオロアルキル基」
　本明細書に記載の「置換もしくは無置換のフルオロアルキル基」は、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している少なくとも１つの水素原子がフッ素原子と置き換わった基を意味し、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している全ての水素原子がフッ素原子で置き換わった基（パーフルオロ基）も含む。「無置換のフルオロアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。「置換のフルオロアルキル基」は、「フルオロアルキル基」の１つ以上の水素原子が置換基と置き換わった基を意味する。尚、本明細書に記載の「置換のフルオロアルキル基」には、「置換のフルオロアルキル基」におけるアルキル鎖の炭素原子に結合する１つ以上の水素原子がさらに置換基と置き換わった基、及び「置換のフルオロアルキル基」における置換基の１つ以上の水素原子がさらに置換基と置き換わった基も含まれる。「無置換のフルオロアルキル基」の具体例としては、前記「アルキル基」（具体例群Ｇ３）における１つ以上の水素原子がフッ素原子と置き換わった基の例等が挙げられる。 ・“Substituted or unsubstituted fluoroalkyl group”
The "substituted or unsubstituted fluoroalkyl group" described in this specification refers to a "substituted or unsubstituted alkyl group" in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group is replaced with a fluorine atom. It also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The number of carbon atoms in the "unsubstituted fluoroalkyl group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein. "Substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced with a substituent. In addition, the "substituted fluoroalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl group" is further replaced with a substituent, and Also included are groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include a group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a fluorine atom.

・「置換もしくは無置換のハロアルキル基」
　本明細書に記載の「置換もしくは無置換のハロアルキル基」は、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している少なくとも１つの水素原子がハロゲン原子と置き換わった基を意味し、「置換もしくは無置換のアルキル基」におけるアルキル基を構成する炭素原子に結合している全ての水素原子がハロゲン原子で置き換わった基も含む。「無置換のハロアルキル基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。「置換のハロアルキル基」は、「ハロアルキル基」の１つ以上の水素原子が置換基と置き換わった基を意味する。尚、本明細書に記載の「置換のハロアルキル基」には、「置換のハロアルキル基」におけるアルキル鎖の炭素原子に結合する１つ以上の水素原子がさらに置換基と置き換わった基、及び「置換のハロアルキル基」における置換基の１つ以上の水素原子がさらに置換基と置き換わった基も含まれる。「無置換のハロアルキル基」の具体例としては、前記「アルキル基」（具体例群Ｇ３）における１つ以上の水素原子がハロゲン原子と置き換わった基の例等が挙げられる。ハロアルキル基をハロゲン化アルキル基と称する場合がある。 ・“Substituted or unsubstituted haloalkyl group”
The "substituted or unsubstituted haloalkyl group" described herein means that at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom. It means a group, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted haloalkyl group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18. "Substituted haloalkyl group" means a group in which one or more hydrogen atoms of the "haloalkyl group" are replaced with a substituent. In addition, the "substituted haloalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl group" is further replaced with a substituent; Also included are groups in which one or more hydrogen atoms of a substituent in the "haloalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include a group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

・「置換もしくは無置換のアルコキシ基」
　本明細書に記載の「置換もしくは無置換のアルコキシ基」の具体例としては、－Ｏ（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。「無置換のアルコキシ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。 ・“Substituted or unsubstituted alkoxy group”
A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkoxy group" described in specific example group G3. "unsubstituted alkyl group". The number of carbon atoms in the "unsubstituted alkoxy group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein.

・「置換もしくは無置換のアルキルチオ基」
　本明細書に記載の「置換もしくは無置換のアルキルチオ基」の具体例としては、－Ｓ（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。「無置換のアルキルチオ基」の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～３０であり、より好ましくは１～１８である。 ・“Substituted or unsubstituted alkylthio group”
A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkylthio group" described in specific example group G3. "unsubstituted alkyl group". Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkylthio group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18.

・「置換もしくは無置換のアリールオキシ基」
　本明細書に記載の「置換もしくは無置換のアリールオキシ基」の具体例としては、－Ｏ（Ｇ１）で表される基であり、ここで、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。「無置換のアリールオキシ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０であり、より好ましくは６～１８である。 ・“Substituted or unsubstituted aryloxy group”
A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryloxy group" described in specific example group G1. or an unsubstituted aryl group. The number of ring carbon atoms in the "unsubstituted aryloxy group" is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.

・「置換もしくは無置換のアリールチオ基」
　本明細書に記載の「置換もしくは無置換のアリールチオ基」の具体例としては、－Ｓ（Ｇ１）で表される基であり、ここで、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。「無置換のアリールチオ基」の環形成炭素数は、本明細書に別途記載のない限り、６～５０であり、好ましくは６～３０であり、より好ましくは６～１８である。 ・“Substituted or unsubstituted arylthio group”
A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted arylthio group" described in the specific example group G1. "Unsubstituted aryl group". The number of ring carbon atoms in the "unsubstituted arylthio group" is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.

・「置換もしくは無置換のトリアルキルシリル基」
　本明細書に記載の「置換もしくは無置換のトリアルキルシリル基」の具体例としては、－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」である。－Ｓｉ（Ｇ３）（Ｇ３）（Ｇ３）における複数のＧ３は、互いに同一であるか、又は異なる。「無置換のトリアルキルシリル基」の各アルキル基の炭素数は、本明細書に別途記載のない限り、１～５０であり、好ましくは１～２０であり、より好ましくは１～６である。 ・“Substituted or unsubstituted trialkylsilyl group”
A specific example of the "substituted or unsubstituted trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a specific example It is a "substituted or unsubstituted alkyl group" described in Group G3. - A plurality of G3's in Si(G3) (G3) (G3) are mutually the same or different. The number of carbon atoms in each alkyl group of the "unsubstituted trialkylsilyl group" is from 1 to 50, preferably from 1 to 20, and more preferably from 1 to 6, unless otherwise specified herein. .

・「置換もしくは無置換のアラルキル基」
　本明細書に記載の「置換もしくは無置換のアラルキル基」の具体例としては、－（Ｇ３）－（Ｇ１）で表される基であり、ここで、Ｇ３は、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」であり、Ｇ１は、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」である。従って、「アラルキル基」は、「アルキル基」の水素原子が置換基としての「アリール基」と置き換わった基であり、「置換のアルキル基」の一態様である。「無置換のアラルキル基」は、「無置換のアリール基」が置換した「無置換のアルキル基」であり、「無置換のアラルキル基」の炭素数は、本明細書に別途記載のない限り、７～５０であり、好ましくは７～３０であり、より好ましくは７～１８である。
　「置換もしくは無置換のアラルキル基」の具体例としては、ベンジル基、１－フェニルエチル基、２－フェニルエチル基、１－フェニルイソプロピル基、２－フェニルイソプロピル基、フェニル－ｔ－ブチル基、α－ナフチルメチル基、１－α－ナフチルエチル基、２－α－ナフチルエチル基、１－α－ナフチルイソプロピル基、２－α－ナフチルイソプロピル基、β－ナフチルメチル基、１－β－ナフチルエチル基、２－β－ナフチルエチル基、１－β－ナフチルイソプロピル基、及び２－β－ナフチルイソプロピル基等が挙げられる。 ・“Substituted or unsubstituted aralkyl group”
A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a group described in specific example group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, an "aralkyl group" is a group in which the hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms in the "unsubstituted aralkyl group" is determined unless otherwise specified herein. , 7 to 50, preferably 7 to 30, more preferably 7 to 18.
Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α - Naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group , 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

　本明細書に記載の置換もしくは無置換のアリール基は、本明細書に別途記載のない限り、好ましくはフェニル基、ｐ－ビフェニル基、ｍ－ビフェニル基、ｏ－ビフェニル基、ｐ－ターフェニル－４－イル基、ｐ－ターフェニル－３－イル基、ｐ－ターフェニル－２－イル基、ｍ－ターフェニル－４－イル基、ｍ－ターフェニル－３－イル基、ｍ－ターフェニル－２－イル基、ｏ－ターフェニル－４－イル基、ｏ－ターフェニル－３－イル基、ｏ－ターフェニル－２－イル基、１－ナフチル基、２－ナフチル基、アントリル基、フェナントリル基、ピレニル基、クリセニル基、トリフェニレニル基、フルオレニル基、９，９’－スピロビフルオレニル基、９，９－ジメチルフルオレニル基、及び９，９－ジフェニルフルオレニル基等である。 The substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl group, unless otherwise specified herein. 4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group , pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group.

　本明細書に記載の置換もしくは無置換の複素環基は、本明細書に別途記載のない限り、好ましくはピリジル基、ピリミジニル基、トリアジニル基、キノリル基、イソキノリル基、キナゾリニル基、ベンゾイミダゾリル基、フェナントロリニル基、カルバゾリル基（１－カルバゾリル基、２－カルバゾリル基、３－カルバゾリル基、４－カルバゾリル基、又は９－カルバゾリル基）、ベンゾカルバゾリル基、アザカルバゾリル基、ジアザカルバゾリル基、ジベンゾフラニル基、ナフトベンゾフラニル基、アザジベンゾフラニル基、ジアザジベンゾフラニル基、ジベンゾチオフェニル基、ナフトベンゾチオフェニル基、アザジベンゾチオフェニル基、ジアザジベンゾチオフェニル基、（９－フェニル）カルバゾリル基（（９－フェニル）カルバゾール－１－イル基、（９－フェニル）カルバゾール－２－イル基、（９－フェニル）カルバゾール－３－イル基、又は（９－フェニル）カルバゾール－４－イル基）、（９－ビフェニリル）カルバゾリル基、（９－フェニル）フェニルカルバゾリル基、ジフェニルカルバゾール－９－イル基、フェニルカルバゾール－９－イル基、フェニルトリアジニル基、ビフェニリルトリアジニル基、ジフェニルトリアジニル基、フェニルジベンゾフラニル基、及びフェニルジベンゾチオフェニル基等である。 The substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, or a phenol group, unless otherwise specified herein. Nanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole -4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyl group These include riazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.

　本明細書において、カルバゾリル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。 In this specification, the carbazolyl group is specifically any of the following groups unless otherwise specified in the specification.

　本明細書において、（９－フェニル）カルバゾリル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。 In this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise stated in the specification.

　前記一般式（ＴＥＭＰ－Ｃｚ１）～（ＴＥＭＰ－Ｃｚ９）中、＊は、結合位置を表す。 In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding position.

　本明細書において、ジベンゾフラニル基、及びジベンゾチオフェニル基は、本明細書に別途記載のない限り、具体的には以下のいずれかの基である。 In this specification, the dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups unless otherwise specified in the specification.

　前記一般式（ＴＥＭＰ－３４）～（ＴＥＭＰ－４１）中、＊は、結合位置を表す。 In the general formulas (TEMP-34) to (TEMP-41), * represents the bonding position.

　本明細書に記載の置換もしくは無置換のアルキル基は、本明細書に別途記載のない限り、好ましくはメチル基、エチル基、プロピル基、イソプロピル基、ｎ－ブチル基、イソブチル基、及びｔ－ブチル基等である。 Unless otherwise specified herein, the substituted or unsubstituted alkyl group described herein is preferably a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t- Butyl group, etc.

・「置換もしくは無置換のアリーレン基」
　本明細書に記載の「置換もしくは無置換のアリーレン基」は、別途記載のない限り、上記「置換もしくは無置換のアリール基」からアリール環上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換のアリーレン基」の具体例（具体例群Ｇ１２）としては、具体例群Ｇ１に記載の「置換もしくは無置換のアリール基」からアリール環上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 ・“Substituted or unsubstituted arylene group”
Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification refers to 2 derived from the above "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aryl ring. It is the basis of valence. As a specific example of the "substituted or unsubstituted arylene group" (specific example group G12), by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1, Examples include divalent groups derived from the derivatives.

・「置換もしくは無置換の２価の複素環基」
　本明細書に記載の「置換もしくは無置換の２価の複素環基」は、別途記載のない限り、上記「置換もしくは無置換の複素環基」から複素環上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換の２価の複素環基」の具体例（具体例群Ｇ１３）としては、具体例群Ｇ２に記載の「置換もしくは無置換の複素環基」から複素環上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 ・“Substituted or unsubstituted divalent heterocyclic group”
Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described herein refers to the "substituted or unsubstituted heterocyclic group" described above, in which one hydrogen atom on the heterocycle is removed. It is a divalent group derived from Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include one hydrogen on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2. Examples include divalent groups derived by removing atoms.

・「置換もしくは無置換のアルキレン基」
　本明細書に記載の「置換もしくは無置換のアルキレン基」は、別途記載のない限り、上記「置換もしくは無置換のアルキル基」からアルキル鎖上の１つの水素原子を除くことにより誘導される２価の基である。「置換もしくは無置換のアルキレン基」の具体例（具体例群Ｇ１４）としては、具体例群Ｇ３に記載の「置換もしくは無置換のアルキル基」からアルキル鎖上の１つの水素原子を除くことにより誘導される２価の基等が挙げられる。 ・“Substituted or unsubstituted alkylene group”
Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification refers to 2 derived from the above "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. It is the basis of valence. As a specific example of a "substituted or unsubstituted alkylene group" (specific example group G14), one hydrogen atom on the alkyl chain is removed from the "substituted or unsubstituted alkyl group" described in specific example group G3. Examples include divalent groups derived from the derivatives.

　本明細書に記載の置換もしくは無置換のアリーレン基は、本明細書に別途記載のない限り、好ましくは下記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－６８）のいずれかの基である。 Unless otherwise stated herein, the substituted or unsubstituted arylene group described herein is preferably a group represented by any of the following general formulas (TEMP-42) to (TEMP-68).

　前記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－５２）中、Ｑ１～Ｑ１０は、それぞれ独立に、水素原子、又は置換基である。
　前記一般式（ＴＥＭＰ－４２）～（ＴＥＭＰ－５２）中、＊は、結合位置を表す。 In the general formulas (TEMP-42) to (TEMP-52), Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
In the general formulas (TEMP-42) to (TEMP-52), * represents the bonding position.

　前記一般式（ＴＥＭＰ－５３）～（ＴＥＭＰ－６２）中、Ｑ１～Ｑ１０は、それぞれ独立に、水素原子、又は置換基である。
　式Ｑ９及びＱ１０は、単結合を介して互いに結合して環を形成してもよい。
　前記一般式（ＴＥＭＰ－５３）～（ＴＥＭＰ－６２）中、＊は、結合位置を表す。 In the general formulas (TEMP-53) to (TEMP-62), Q 1 to Q 10 are each independently a hydrogen atom or a substituent.
Formulas Q 9 and Q 10 may be bonded to each other via a single bond to form a ring.
In the general formulas (TEMP-53) to (TEMP-62), * represents the bonding position.

　前記一般式（ＴＥＭＰ－６３）～（ＴＥＭＰ－６８）中、Ｑ１～Ｑ８は、それぞれ独立に、水素原子、又は置換基である。
　前記一般式（ＴＥＭＰ－６３）～（ＴＥＭＰ－６８）中、＊は、結合位置を表す。 In the general formulas (TEMP-63) to (TEMP-68), Q 1 to Q 8 are each independently a hydrogen atom or a substituent.
In the general formulas (TEMP-63) to (TEMP-68), * represents the bonding position.

　本明細書に記載の置換もしくは無置換の２価の複素環基は、本明細書に別途記載のない限り、好ましくは下記一般式（ＴＥＭＰ－６９）～（ＴＥＭＰ－１０２）のいずれかの基である。 The substituted or unsubstituted divalent heterocyclic group described herein is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein. It is.

　前記一般式（ＴＥＭＰ－６９）～（ＴＥＭＰ－８２）中、Ｑ１～Ｑ９は、それぞれ独立に、水素原子、又は置換基である。前記一般式（ＴＥＭＰ－６９）～（ＴＥＭＰ－８２）中、＊は、結合位置を表す。 In the general formulas (TEMP-69) to (TEMP-82), Q 1 to Q 9 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-69) to (TEMP-82), * represents the bonding position.

　前記一般式（ＴＥＭＰ－８３）～（ＴＥＭＰ－１０２）中、Ｑ１～Ｑ８は、それぞれ独立に、水素原子、又は置換基である。前記一般式（ＴＥＭＰ－８３）～（ＴＥＭＰ－１０２）中、＊は、結合位置を表す。 In the general formulas (TEMP-83) to (TEMP-102), Q 1 to Q 8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-83) to (TEMP-102), * represents the bonding position.

　以上が、「本明細書に記載の置換基」についての説明である。 The above is an explanation of the "substituents described in this specification."

・「結合して環を形成する場合」
　本明細書において、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合せず」という場合は、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合と、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合と、「隣接する２つ以上からなる組の１組以上が、互いに結合しない」場合と、を意味する。
　本明細書における、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合、及び「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合（以下、これらの場合をまとめて「結合して環を形成する場合」と称する場合がある。）について、以下、
説明する。母骨格がアントラセン環である下記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物の場合を例として説明する。 ・"When combining to form a ring"
In the present specification, "one or more pairs of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring." or do not bond to each other'' means ``one or more pairs of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle''; One or more pairs of two or more adjacent groups bond to each other to form a substituted or unsubstituted condensed ring, and one or more pairs of two or more adjacent groups do not bond to each other. ” means if and.
In this specification, when "one or more sets of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted monocycle" and "one or more sets of two or more adjacent rings are combined with each other to form a substituted or unsubstituted monocycle" Regarding the case where "a pair or more are combined with each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "a case where they are combined to form a ring"), the following ,
explain. The case of an anthracene compound represented by the following general formula (TEMP-103) whose parent skeleton is an anthracene ring will be explained as an example.

　例えば、Ｒ９２１～Ｒ９３０のうちの「隣接する２つ以上からなる組の１組以上が、互いに結合して、環を形成する」場合において、１組となる隣接する２つからなる組とは、Ｒ９２１とＲ９２２との組、Ｒ９２２とＲ９２３との組、Ｒ９２３とＲ９２４との組、Ｒ９２４とＲ９３０との組、Ｒ９３０とＲ９２５との組、Ｒ９２５とＲ９２６との組、Ｒ９２６とＲ９２７との組、Ｒ９２７とＲ９２８との組、Ｒ９２８とＲ９２９との組、並びにＲ９２９とＲ９２１との組である。 For example, in the case where "one or more of the sets of two or more adjacent R 921 to R 930 are bonded to each other to form a ring", the set of two or more adjacent R 930 is one set. is a set of R 921 and R 922 , a set of R 922 and R 923 , a set of R 923 and R 924 , a set of R 924 and R 930 , a set of R 930 and R 925 , a set of R 925 and A set of R 926 , a set of R 926 and R 927 , a set of R 927 and R 928 , a set of R 928 and R 929 , and a set of R 929 and R 921 .

　上記「１組以上」とは、上記隣接する２つ以上からなる組の２組以上が同時に環を形成してもよいことを意味する。例えば、Ｒ９２１とＲ９２２とが互いに結合して環ＱＡを形成し、同時にＲ９２５とＲ９２６とが互いに結合して環ＱＢを形成した場合は、前記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物は、下記一般式（ＴＥＭＰ－１０４）で表される。 The above-mentioned "one or more sets" means that two or more sets of the above-mentioned two or more adjacent sets may form a ring at the same time. For example, when R 921 and R 922 combine with each other to form ring Q A , and at the same time R 925 and R 926 combine with each other to form ring Q B , the above general formula (TEMP-103) The anthracene compound represented is represented by the following general formula (TEMP-104).

　「隣接する２つ以上からなる組」が環を形成する場合とは、前述の例のように隣接する「２つ」からなる組が結合する場合だけではなく、隣接する「３つ以上」からなる組が結合する場合も含む。例えば、Ｒ９２１とＲ９２２とが互いに結合して環ＱＡを形成し、かつ、Ｒ９２２とＲ９２３とが互いに結合して環ＱＣを形成し、互いに隣接する３つ（Ｒ９２１、Ｒ９２２及びＲ９２３）からなる組が互いに結合して環を形成して、アントラセン母骨格に縮合する場合を意味し、この場合、前記一般式（ＴＥＭＰ－１０３）で表されるアントラセン化合物は、下記一般式（ＴＥＭＰ－１０５）で表される。下記一般式（ＴＥＭＰ－１０５）において、環ＱＡ及び環ＱＣは、Ｒ９２２を共有する。 The case where "a set of two or more adjacent items" forms a ring is not only the case where a set of "two" adjacent items are combined as in the example above, but also the case where a set of "three or more adjacent items" form a ring. This also includes the case where two sets are combined. For example, R 921 and R 922 combine with each other to form a ring Q A , R 922 and R 923 combine with each other to form a ring Q C , and the three adjacent to each other (R 921 , R 922 and R 923 ) combine with each other to form a ring and are condensed to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is as follows: It is represented by the general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .

　形成される「単環」、又は「縮合環」は、形成された環のみの構造として、飽和の環であっても不飽和の環であってもよい。「隣接する２つからなる組の１組」が「単環」、又は「縮合環」を形成する場合であっても、当該「単環」、又は「縮合環」は、飽和の環、又は不飽和の環を形成することができる。例えば、前記一般式（ＴＥＭＰ－１０４）において形成された環ＱＡ及び環ＱＢは、それぞれ、「単環」又は「縮合環」である。また、前記一般式（ＴＥＭＰ－１０５）において形成された環ＱＡ、及び環ＱＣは、「縮合環」である。前記一般式（ＴＥＭＰ－１０５）の環ＱＡと環ＱＣとは、環ＱＡと環ＱＣとが縮合することによって縮合環となっている。前記一般式（ＴＭＥＰ－１０４）の環ＱＡがベンゼン環であれば、環ＱＡは、単環である。前記一般式（ＴＭＥＰ－１０４）の環ＱＡがナフタレン環であれば、環ＱＡは、縮合環である。 The "single ring" or "fused ring" that is formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even if "one set of two adjacent rings" forms a "monocycle" or "fused ring," the "monocycle" or "fused ring" is a saturated ring, or Can form unsaturated rings. For example, ring Q A and ring Q B formed in the general formula (TEMP-104) are each a "monocyclic ring" or a "fused ring." Furthermore, the ring Q A and the ring Q C formed in the general formula (TEMP-105) are "fused rings". Ring Q A and ring Q C in the general formula (TEMP-105) are a condensed ring due to the condensation of ring Q A and ring Q C. When ring Q A in the general formula (TMEP-104) is a benzene ring, ring Q A is a monocyclic ring. When ring Q A in the general formula (TMEP-104) is a naphthalene ring, ring Q A is a fused ring.

　「不飽和の環」は、芳香族炭化水素環、芳香族複素環、環構造中に不飽和結合を有する脂肪族炭化水素環及び環構造中に不飽和結合を有する非芳香族複素環からなる群から選択される少なくともいずれかの環である。不飽和の環が当該環構造中に有する不飽和結合は、二重結合及び三重結合の一方もしくは両方である。環構造中に不飽和結合を有する脂肪族炭化水素環は、例えば、シクロヘキセン及びシクロヘキサジエン等である。環構造中に不飽和結合を有する非芳香族複素環は、例えば、ジヒドロピラン、イミダゾリン、ピラゾリン、キノリジン、インドリン及びイソインドリン等である。 "Unsaturated ring" refers to an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring having an unsaturated bond in the ring structure, and a non-aromatic heterocycle having an unsaturated bond in the ring structure. At least one ring selected from the group. The unsaturated bond that the unsaturated ring has in the ring structure is one or both of a double bond and a triple bond. Examples of the aliphatic hydrocarbon ring having an unsaturated bond in the ring structure include cyclohexene and cyclohexadiene. Examples of the non-aromatic heterocycle having an unsaturated bond in the ring structure include dihydropyran, imidazoline, pyrazoline, quinolidine, indoline, and isoindoline.

　「飽和の環」は、不飽和結合を有しない脂肪族炭化水素環及び不飽和結合を有しない非芳香族複素環から選択される少なくともいずれかの環である。飽和の環は、当該環構造中に二重結合及び三重結合を有さない。
　芳香族炭化水素環の具体例としては、具体例群Ｇ１において具体例として挙げられた基が水素原子によって終端された構造が挙げられる。
　芳香族複素環の具体例としては、具体例群Ｇ２において具体例として挙げられた芳香族複素環基が水素原子によって終端された構造が挙げられる。
　脂肪族炭化水素環の具体例としては、具体例群Ｇ６において具体例として挙げられた基が水素原子によって終端された構造が挙げられる。
　「環を形成する」とは、母骨格の複数の原子のみ、あるいは母骨格の複数の原子とさらに１以上の任意の原子で環を形成することを意味する。例えば、前記一般式（ＴＥＭＰ－１０４）に示す、Ｒ９２１とＲ９２２とが互いに結合して形成された環ＱＡは、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２が結合するアントラセン骨格の炭素原子と、１以上の任意の原子とで形成する環を意味する。具体例としては、Ｒ９２１とＲ９２２とで環ＱＡを形成する場合において、Ｒ９２１が結合するアントラセン骨格の炭素原子と、Ｒ９２２とが結合するアントラセン骨格の炭素原子と、４つの炭素原子とで単環の不飽和の環を形成する場合、Ｒ９２１とＲ９２２とで形成する環は、ベンゼン環である。 The "saturated ring" is at least one ring selected from an aliphatic hydrocarbon ring having no unsaturated bond and a non-aromatic heterocycle having no unsaturated bond. A saturated ring has no double or triple bonds in the ring structure.
Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G1 are terminated with hydrogen atoms.
Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic group listed as a specific example in specific example group G2 is terminated with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G6 are terminated with hydrogen atoms.
"Form a ring" means to form a ring with only a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more arbitrary atoms. For example, the ring Q A shown in the general formula (TEMP-104) formed by R 921 and R 922 bonding to each other is a carbon atom of the anthracene skeleton to which R 921 is bonded, and an anthracene bond to which R 922 is bonded. It means a ring formed by a carbon atom of the skeleton and one or more arbitrary atoms. As a specific example, when R 921 and R 922 form a ring Q A , the carbon atom of the anthracene skeleton to which R 921 is bonded, the carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms. When R 921 and R 922 form a monocyclic unsaturated ring, the ring formed by R 921 and R 922 is a benzene ring.

　ここで、「任意の原子」は、本明細書に別途記載のない限り、好ましくは、炭素原子、窒素原子、酸素原子、及び硫黄原子からなる群から選択される少なくとも１種の原子である。任意の原子において（例えば、炭素原子、又は窒素原子の場合）、環を形成しない結合は、水素原子等で終端されてもよいし、後述する「任意の置換基」で置換されてもよい。炭素原子以外の任意の原子を含む場合、形成される環は複素環である。
　単環または縮合環を構成する「１以上の任意の原子」は、本明細書に別途記載のない限り、好ましくは２個以上１５個以下であり、より好ましくは３個以上１２個以下であり、さらに好ましくは３個以上５個以下である。
　本明細書に別途記載のない限り、「単環」、及び「縮合環」のうち、好ましくは「単環」である。
　本明細書に別途記載のない限り、「飽和の環」、及び「不飽和の環」のうち、好ましくは「不飽和の環」である。
　本明細書に別途記載のない限り、「単環」は、好ましくはベンゼン環である。
　本明細書に別途記載のない限り、「不飽和の環」は、好ましくはベンゼン環である。
　「隣接する２つ以上からなる組の１組以上」が、「互いに結合して、置換もしくは無置換の単環を形成する」場合、又は「互いに結合して、置換もしくは無置換の縮合環を形成する」場合、本明細書に別途記載のない限り、好ましくは、隣接する２つ以上からなる組の１組以上が、互いに結合して、母骨格の複数の原子と、１個以上１５個以下の炭素原子、窒素原子、酸素原子、及び硫黄原子からなる群から選択される少なくとも１種の原子とからなる置換もしくは無置換の「不飽和の環」を形成する。 Here, unless otherwise specified herein, "any atom" is preferably at least one atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom. In any atom (for example, in the case of a carbon atom or a nitrogen atom), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When it contains any atoms other than carbon atoms, the ring formed is a heterocycle.
Unless otherwise specified herein, "one or more arbitrary atoms" constituting a monocyclic ring or a condensed ring are preferably 2 to 15 atoms, more preferably 3 to 12 atoms. , more preferably 3 or more and 5 or less.
Unless otherwise specified herein, "monocycle" is preferred among "monocycle" and "fused ring."
Unless otherwise specified herein, the "unsaturated ring" is preferred between the "saturated ring" and the "unsaturated ring".
Unless otherwise stated herein, a "monocycle" is preferably a benzene ring.
Unless otherwise stated herein, an "unsaturated ring" is preferably a benzene ring.
When "one or more pairs of two or more adjacent groups" are "bonded with each other to form a substituted or unsubstituted monocycle" or "bonded with each other to form a substituted or unsubstituted fused ring" In the case of "forming", unless otherwise specified herein, preferably, one or more of the pairs of two or more adjacent atoms are bonded to each other to form a bond with a plurality of atoms of the parent skeleton and one or more of the 15 or more atoms. A substituted or unsubstituted "unsaturated ring" is formed with at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

　上記の「単環」、又は「縮合環」が置換基を有する場合の置換基は、例えば後述する「任意の置換基」である。上記の「単環」、又は「縮合環」が置換基を有する場合の置換基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基である。
　上記の「飽和の環」、又は「不飽和の環」が置換基を有する場合の置換基は、例えば後述する「任意の置換基」である。上記の「飽和の環」、又は「不飽和の環」が置換基を有する場合の置換基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基である。
　以上が、「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の単環を形成する」場合、及び「隣接する２つ以上からなる組の１組以上が、互いに結合して、置換もしくは無置換の縮合環を形成する」場合（「結合して環を形成する場合」）についての説明である。 When the above-mentioned "single ring" or "fused ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described below. Specific examples of the substituent in the case where the above-mentioned "single ring" or "fused ring" has a substituent are the substituents described in the section of "Substituent described herein" above.
When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described below. When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, specific examples of the substituent are the substituents described in the section of "Substituent described herein" above. .
The above applies to cases in which "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle" and "one or more sets of two or more adjacent groups" are combined with each other to form a substituted or unsubstituted condensed ring ("the case where they are combined to form a ring").

・「置換もしくは無置換の」という場合の置換基
　本明細書における一実施形態においては、前記「置換もしくは無置換の」という場合の置換基（本明細書において、「任意の置換基」と呼ぶことがある。）は、例えば、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ９０１）（Ｒ９０２）（Ｒ９０３）、
－Ｏ－（Ｒ９０４）、
－Ｓ－（Ｒ９０５）、
－Ｎ（Ｒ９０６）（Ｒ９０７）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、及び
無置換の環形成原子数５～５０の複素環基からなる群から選択される基等であり、
　ここで、Ｒ９０１～Ｒ９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は置換もしくは無置換の環形成原子数５～５０の複素環基である。
　Ｒ９０１が２個以上存在する場合、２個以上のＲ９０１は、互いに同一であるか、又は異なり、
　Ｒ９０２が２個以上存在する場合、２個以上のＲ９０２は、互いに同一であるか、又は異なり、
　Ｒ９０３が２個以上存在する場合、２個以上のＲ９０３は、互いに同一であるか、又は異なり、
　Ｒ９０４が２個以上存在する場合、２個以上のＲ９０４は、互いに同一であるか、又は異なり、
　Ｒ９０５が２個以上存在する場合、２個以上のＲ９０５は、互いに同一であるか、又は異なり、
　Ｒ９０６が２個以上存在する場合、２個以上のＲ９０６は、互いに同一であるか、又は異なり、
　Ｒ９０７が２個以上存在する場合、２個以上のＲ９０７は、互いに同一であるか又は異なる。 ・Substituent in the case of "substituted or unsubstituted" In one embodiment in this specification, the substituent in the case of "substituted or unsubstituted" (herein referred to as "arbitrary substituent") For example,
unsubstituted alkyl group having 1 to 50 carbon atoms,
unsubstituted alkenyl group having 2 to 50 carbon atoms,
unsubstituted alkynyl group having 2 to 50 carbon atoms,
an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R 901 )(R 902 )(R 903 ),
-O-(R 904 ),
-S- (R 905 ),
-N(R 906 )(R 907 ),
Halogen atom, cyano group, nitro group,
A group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms,
Here, R 901 to R 907 are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
When two or more R 901s exist, the two or more R 901s are the same or different,
When two or more R 902s exist, the two or more R 902s are the same or different,
When two or more R 903s exist, the two or more R 903s are the same or different,
When two or more R 904s exist, the two or more R 904s are the same or different,
When two or more R 905s exist, the two or more R 905s are the same or different,
When two or more R 906s exist, the two or more R 906s are the same or different,
When two or more R 907s exist, the two or more R 907s are the same or different.

　一実施形態においては、前記「置換もしくは無置換の」という場合の置換基は、
炭素数１～５０のアルキル基、
環形成炭素数６～５０のアリール基、及び
環形成原子数５～５０の複素環基からなる群から選択される基である。 In one embodiment, the substituent in the case of "substituted or unsubstituted" is
an alkyl group having 1 to 50 carbon atoms,
A group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.

　一実施形態においては、前記「置換もしくは無置換の」という場合の置換基は、
炭素数１～１８のアルキル基、
環形成炭素数６～１８のアリール基、及び
環形成原子数５～１８の複素環基からなる群から選択される基である。 In one embodiment, the substituent in the case of "substituted or unsubstituted" is
an alkyl group having 1 to 18 carbon atoms,
A group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.

　上記任意の置換基の各基の具体例は、上述した「本明細書に記載の置換基」の項で説明した置換基の具体例である。 Specific examples of each group of the above-mentioned arbitrary substituents are the specific examples of the substituents described in the section of "Substituents described in this specification" above.

　本明細書において別途記載のない限り、隣接する任意の置換基同士で、「飽和の環」、又は「不飽和の環」を形成してもよく、好ましくは、置換もしくは無置換の飽和の５員環、置換もしくは無置換の飽和の６員環、置換もしくは無置換の不飽和の５員環、又は置換もしくは無置換の不飽和の６員環を形成し、より好ましくは、ベンゼン環を形成する。
　本明細書において別途記載のない限り、任意の置換基は、さらに置換基を有してもよい。任意の置換基がさらに有する置換基としては、上記任意の置換基と同様である。
　任意の置換基が複数存在する場合、複数の任意の置換基は、互いに同一であるか又は異なる。 Unless otherwise specified in this specification, any adjacent substituents may form a "saturated ring" or "unsaturated ring", preferably a substituted or unsubstituted saturated ring. Forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring do.
Unless otherwise specified herein, any substituent may further have a substituent. The substituents that the arbitrary substituents further have are the same as the above arbitrary substituents.
When a plurality of arbitrary substituents exist, the plurality of arbitrary substituents are the same or different from each other.

　本明細書において、「ＡＡ～ＢＢ」を用いて表される数値範囲は、「ＡＡ～ＢＢ」の前に記載される数値ＡＡを下限値とし、「ＡＡ～ＢＢ」の後に記載される数値ＢＢを上限値として含む範囲を意味する。 In this specification, the numerical range expressed using "AA-BB" has the numerical value AA written before "AA-BB" as the lower limit, and the numerical value BB written after "AA-BB". means a range that includes as an upper limit value.

〔第一実施形態〕
　本発明の第一実施形態に係る有機ＥＬ素子の構成について説明する。
　有機ＥＬ素子は、陽極および陰極の両電極間に有機層を備える。この有機層は、有機化合物で構成される層を少なくとも一つ含む。あるいは、この有機層は、有機化合物で構成される複数の層が積層されてなる。有機層は、無機化合物をさらに含んでいてもよい。本実施形態の有機ＥＬ素子において、有機層のうち少なくとも一層は、発光層である。ゆえに、有機層は、例えば、一つの発光層で構成されていてもよいし、有機ＥＬ素子に採用され得る層を含んでいてもよい。有機ＥＬ素子に採用され得る層としては、特に限定されないが、例えば、正孔注入層、正孔輸送層、電子注入層、電子輸送層、及び障壁層からなる群から選択される少なくともいずれかの層が挙げられる。
　本実施形態の有機ＥＬ素子は、陽極と陰極との間に含まれる発光層を有する。 [First embodiment]
The structure of the organic EL element according to the first embodiment of the present invention will be explained.
An organic EL element includes an organic layer between an anode and a cathode. This organic layer includes at least one layer composed of an organic compound. Alternatively, this organic layer is formed by laminating a plurality of layers made of organic compounds. The organic layer may further contain an inorganic compound. In the organic EL device of this embodiment, at least one of the organic layers is a light emitting layer. Therefore, the organic layer may be composed of, for example, one light emitting layer, or may include layers that can be employed in an organic EL element. Layers that can be used in organic EL devices are not particularly limited, but for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer. Examples include layers.
The organic EL element of this embodiment has a light emitting layer included between an anode and a cathode.

　本実施形態の有機ＥＬ素子は、陽極と、陰極と、前記陽極と前記陰極との間に含まれる発光層と、を有し、前記発光層は、下記一般式（１－１）または（１－２）で表される化合物Ｍ３と、遅延蛍光性の化合物Ｍ２と、を含み、前記化合物Ｍ３と前記化合物Ｍ２とは構造が異なり、前記化合物Ｍ３の一重項エネルギーＳ１（Ｍ３）と、前記化合物Ｍ２の一重項エネルギーＳ１（Ｍ２）とが、下記数式（数１）の関係を満たす。
　　　Ｓ１（Ｍ３）＞Ｓ１（Ｍ２）　　　（数１） The organic EL element of this embodiment has an anode, a cathode, and a light emitting layer included between the anode and the cathode, and the light emitting layer has the following general formula (1-1) or (1). -2) and a delayed fluorescent compound M2, the compound M3 and the compound M2 have different structures, and the singlet energy S 1 (M3) of the compound M3, The singlet energy S 1 (M2) of compound M2 satisfies the relationship of the following formula (Equation 1).
S 1 (M3)>S 1 (M2) (Math. 1)

　本発明者らは、前記一般式（１－１）または（１－２）で表される化合物Ｍ３（本実施形態に係る化合物Ｍ３）を、遅延蛍光性の化合物Ｍ２と共に発光層に含ませることにより、高性能の有機ＥＬ素子を実現できることを見出した。
　本実施形態に係る化合物Ｍ３は、発光層に適切な量の正孔を供給するベンゾフラノカルバゾール若しくはベンゾチエノカルバゾールと、耐久性の高いジベンゾフラン若しくはジベンゾチオフェンとを、共役長の短いメタ結合ビフェニレン若しくはオルト結合ビフェニレンを介して結合させた化合物である。本実施形態に係る化合物Ｍ３は、高い三重項エネルギーを示すため、遅延蛍光性の化合物の三重項エネルギーを十分閉じ込めることができる。
　よって、本実施形態によれば、高性能の有機ＥＬ素子を実現できる。
　本実施形態の一態様によれば、有機ＥＬ素子が高効率で発光する。
　本実施形態の一態様によれば、有機ＥＬ素子が長寿命化する。 The present inventors have proposed that the compound M3 represented by the general formula (1-1) or (1-2) (compound M3 according to the present embodiment) be included in the light-emitting layer together with the delayed fluorescent compound M2. We have discovered that a high-performance organic EL device can be realized by this method.
Compound M3 according to the present embodiment combines benzofuranocarbazole or benzothienocarbazole, which supplies an appropriate amount of holes to the light emitting layer, and highly durable dibenzofuran or dibenzothiophene, into meta-bonded biphenylene or ortho-bonded biphenylene having a short conjugation length. This is a compound bound via a bound biphenylene. Since the compound M3 according to the present embodiment exhibits high triplet energy, it is possible to sufficiently confine the triplet energy of the delayed fluorescent compound.
Therefore, according to this embodiment, a high-performance organic EL element can be realized.
According to one aspect of this embodiment, the organic EL element emits light with high efficiency.
According to one aspect of the present embodiment, the life of the organic EL element is extended.

　図１に、本実施形態における有機ＥＬ素子の一例の概略構成を示す。
　有機ＥＬ素子１は、透光性の基板２と、陽極３と、陰極４と、陽極３と陰極４との間に配置された有機層１０と、を含む。有機層１０は、陽極３側から順に、正孔注入層６、正孔輸送層７、発光層５、電子輸送層８、および電子注入層９が、この順番で積層されて構成される。 FIG. 1 shows a schematic configuration of an example of an organic EL element in this embodiment.
The organic EL element 1 includes a transparent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is configured by stacking a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order from the anode 3 side.

　発光層５は、金属錯体を含んでもよい。
　発光層５は、燐光発光性材料（ドーパント材料）を含まないことが好ましい。
　発光層５は、重金属錯体及び燐光発光性の希土類金属錯体を含まないことが好ましい。ここで、重金属錯体としては、例えば、イリジウム錯体、オスミウム錯体、及び白金錯体等が挙げられる。
　また、発光層５は、金属錯体を含まないことも好ましい。
　本実施形態の有機ＥＬ素子１において、発光層５は、遅延蛍光性の化合物Ｍ２と、一般式（１－１）または（１－２）で表される化合物Ｍ３と、を含む。
　この態様の場合、化合物Ｍ２は、ドーパント材料（ゲスト材料、エミッター、発光材料と称する場合もある。）であることが好ましく、化合物Ｍ３は、ホスト材料（マトリックス材料と称する場合もある。）であることが好ましい。
　化合物Ｍ３は、遅延蛍光性の化合物でもよいし、遅延蛍光性を示さない化合物でもよい。 The light emitting layer 5 may contain a metal complex.
It is preferable that the light emitting layer 5 does not contain a phosphorescent material (dopant material).
The light emitting layer 5 preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Here, examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.
Moreover, it is also preferable that the light-emitting layer 5 does not contain a metal complex.
In the organic EL device 1 of this embodiment, the light emitting layer 5 includes a delayed fluorescent compound M2 and a compound M3 represented by the general formula (1-1) or (1-2).
In this embodiment, the compound M2 is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a luminescent material), and the compound M3 is preferably a host material (sometimes referred to as a matrix material). It is preferable.
Compound M3 may be a compound that exhibits delayed fluorescence or may be a compound that does not exhibit delayed fluorescence.

　以下、本実施形態の有機ＥＬ素子の構成について詳細に説明する。以下、符号の記載を省略する。 Hereinafter, the configuration of the organic EL element of this embodiment will be described in detail. Hereinafter, the description of the symbols will be omitted.

＜発光層＞
（化合物Ｍ３）
　本実施形態における発光層は、下記一般式（１－１）または（１－２）で表される化合物Ｍ３を含む。
　本実施形態における化合物Ｍ３は、熱活性化遅延蛍光性の化合物でもよいし、熱活性化遅延蛍光性を示さない化合物でもよいが、熱活性遅延蛍光性を示さない化合物であることが好ましい。 <Light-emitting layer>
(Compound M3)
The light-emitting layer in this embodiment includes a compound M3 represented by the following general formula (1-1) or (1-2).
Compound M3 in this embodiment may be a compound that exhibits heat-activated delayed fluorescence or a compound that does not exhibit heat-activated delayed fluorescence, but is preferably a compound that does not exhibit thermally-activated delayed fluorescence.

（前記一般式（１－１）及び（１－２）において、
　Ａは、下記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）のいずれかで表される基であり、
　Ｌ１及びＬ２は、それぞれ独立に、
　　単結合、又は
　　置換もしくは無置換の環形成炭素数６～５０のアリーレン基であり、
　Ｙ１は、酸素原子又は硫黄原子であり、
　Ｒ２１～Ｒ２８のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　Ｒ１００並びに、前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８は、それぞれ独立に、
　　水素原子、
　　ハロゲン原子、
　　シアノ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、
　　置換もしくは無置換の炭素数１～３０のアルキル基、
　　置換もしくは無置換の炭素数１～３０のハロゲン化アルキル基、
　　置換もしくは無置換の環形成炭素数３～３０のシクロアルキル基、
　　置換もしくは無置換の炭素数２～３０のアルケニル基、
　　置換もしくは無置換の炭素数２～３０のアルキニル基、
　　置換もしくは無置換の炭素数３～３０のアルキルシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールホスホリル基、
　　ヒドロキシ基、
　　置換もしくは無置換の炭素数１～３０のアルコキシ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリールオキシ基、
　　－Ｎ（Ｒｚ）２で表される基、
　　チオール基、
　　置換もしくは無置換の炭素数１～３０のアルキルチオ基、
　　置換もしくは無置換の環形成炭素数７～３０のアラルキル基、
　　置換ゲルマニウム基、
　　置換ホスフィンオキシド基、
　　ニトロ基、
　　置換ボリル基、又は
　　置換もしくは無置換の環形成炭素数６～３０のアリールチオ基であり、
　Ｒｚは、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、又は
　　置換もしくは無置換の炭素数１～３０のアルキル基であり、
　－Ｎ（Ｒｚ）２における２つのＲｚは、互いに同一であるか、又は異なり、
　複数のＲ１００は、互いに同一であるか、又は異なり、
　前記一般式（１－１）及び（１－２）中、＊は、Ｒ２１～Ｒ２４が結合する六員環の炭素原子のいずれか１つとの結合位置を表す。） (In the general formulas (1-1) and (1-2),
A is a group represented by any of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
L 1 and L 2 are each independently,
A single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,
Y 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 21 to R 28 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 100 and R 21 to R 28 that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring are each independently,
hydrogen atom,
halogen atom,
cyano group,
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
Substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
Substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,
hydroxy group,
a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
-N(Rz) a group represented by 2 ,
thiol group,
a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms,
substituted germanium group,
substituted phosphine oxide group,
nitro group,
A substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
Rz is
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
-N(Rz) The two Rz in 2 are the same or different,
A plurality of R 100s are the same or different from each other,
In the general formulas (1-1) and (1-2), * represents the bonding position to any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded. )

（前記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）において、
　Ｘ１は、酸素原子又は硫黄原子であり、
　Ｒ１１～Ｒ２０のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ１１～Ｒ２０は、それぞれ独立に、前記一般式（１－１）及び（１－２）における前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８と同義であり、＊は、結合位置を表す。） (In the general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
X 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 11 to R 20 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 11 to R 20 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently represented by the general formulas (1-1) and (1-2). It has the same meaning as R 21 to R 28 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, and * represents a bonding position. )

　前記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）において、
　Ｌ１が単結合であり、Ｌ２がアリーレン基である場合、＊は、Ｌ２との結合位置を表し、
　Ｌ１がアリーレン基であり、Ｌ２が単結合である場合、＊は、Ｌ１との結合位置を表し、
　Ｌ１及びＬ２がアリーレン基である場合、＊は、Ｌ１との結合位置を表し、
　Ｌ１及びＬ２が単結合である場合、＊は、六員環の炭素原子との結合位置を表す。 In the general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
When L 1 is a single bond and L 2 is an arylene group, * represents the bonding position with L 2 ,
When L 1 is an arylene group and L 2 is a single bond, * represents the bonding position with L 1 ,
When L 1 and L 2 are arylene groups, * represents the bonding position with L 1 ,
When L 1 and L 2 are single bonds, * represents the bonding position with the carbon atom of the six-membered ring.

　本実施形態において、化合物Ｍ３は、前記一般式（１－１）で表される化合物であることが好ましい。
　本実施形態において、化合物Ｍ３としての前記一般式（１－１）で表される化合物は、下記一般式（１００－１）、（１００－２）、（１００－３）又は（１００－５）で表される。 In this embodiment, compound M3 is preferably a compound represented by the general formula (1-1).
In this embodiment, the compound represented by the general formula (1-1) as compound M3 is represented by the following general formula (100-1), (100-2), (100-3) or (100-5). It is expressed as

（前記一般式（１００－１）、（１００－２）、（１００－３）及び（１００－５）において、Ａ、Ｌ１、Ｌ２、Ｙ１、Ｒ２１～Ｒ２８及びＲ１００は、それぞれ独立に、前記一般式（１－１）におけるＡ、Ｌ１、Ｌ２、Ｙ１、Ｒ２１～Ｒ２８及びＲ１００と同義である。） (In the general formulas (100-1), (100-2), (100-3) and (100-5), A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 are Each independently has the same meaning as A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 in the general formula (1-1).)

　本実施形態において、化合物Ｍ３としての前記一般式（１－２）で表される化合物は、下記一般式（１００－４Ａ）、（１００－４Ｂ）、（１００－４Ｃ）、又は（１００－４Ｄ）で表される。 In this embodiment, the compound represented by the general formula (1-2) as compound M3 is the following general formula (100-4A), (100-4B), (100-4C), or (100-4D). ).

（前記一般式（１００－４Ａ）、（１００－４Ｂ）、（１００－４Ｃ）及び（１００－４Ｄ）において、Ａ、Ｌ１、Ｌ２、Ｙ１、Ｒ２１～Ｒ２８及びＲ１００は、それぞれ独立に、前記一般式（１－２）におけるＡ、Ｌ１、Ｌ２、Ｙ１、Ｒ２１～Ｒ２８及びＲ１００と同義である。） (In the general formulas (100-4A), (100-4B), (100-4C) and (100-4D), A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 are Each independently has the same meaning as A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 in the general formula (1-2).)

　一実施形態に係る化合物Ｍ３において、Ｌ１及びＬ２は、それぞれ独立に、単結合、又は置換もしくは無置換のフェニレン基である。
　一実施形態に係る化合物Ｍ３において、Ｌ１及びＬ２は、単結合である。 In compound M3 according to one embodiment, L 1 and L 2 are each independently a single bond or a substituted or unsubstituted phenylene group.
In compound M3 according to one embodiment, L 1 and L 2 are single bonds.

　一実施形態に係る化合物Ｍ３において、Ａは、前記一般式（１１Ｆ）で表される基である。
　一実施形態に係る化合物Ｍ３において、Ａは、前記一般式（１１Ｄ）で表される基である。 In compound M3 according to one embodiment, A is a group represented by the general formula (11F).
In compound M3 according to one embodiment, A is a group represented by the general formula (11D).

　一実施形態に係る化合物Ｍ３において、Ｘ１は、硫黄原子である。
　一実施形態に係る化合物Ｍ３において、Ｘ１は、酸素原子である。
　一実施形態に係る化合物Ｍ３において、Ｙ１は、酸素原子である。
　一実施形態に係る化合物Ｍ３において、Ｘ１は硫黄原子であり、Ｙ１は酸素原子である。一実施形態に係る化合物Ｍ３において、Ｘ１及びＹ１は、酸素原子である。 In compound M3 according to one embodiment, X 1 is a sulfur atom.
In compound M3 according to one embodiment, X 1 is an oxygen atom.
In compound M3 according to one embodiment, Y 1 is an oxygen atom.
In compound M3 according to one embodiment, X 1 is a sulfur atom and Y 1 is an oxygen atom. In compound M3 according to one embodiment, X 1 and Y 1 are oxygen atoms.

　一実施形態に係る化合物Ｍ３において、Ｒ２１～Ｒ２８のうちの隣接する２つ以上からなる組が互いに結合しない。
　一実施形態に係る化合物Ｍ３において、Ｒ２１～Ｒ２８は、それぞれ独立に、水素原子、置換もしくは無置換の環形成炭素数６～３０のアリール基（好ましくは置換もしくは無置換のフェニル基）である。
　一実施形態に係る化合物Ｍ３において、Ｒ２１～Ｒ２８は、それぞれ独立に、水素原子、置換もしくは無置換のフェニル基、置換もしくは無置換のビフェニル基、置換もしくは無置換のカルバゾリル基、又は置換もしくは無置換のジベンゾフラニル基である。
　一実施形態に係る化合物Ｍ３において、Ｒ２１～Ｒ２８は水素原子である。
　一実施形態に係る化合物Ｍ３において、Ｒ２１～Ｒ２８の少なくとも１つは重水素原子である。 In compound M3 according to one embodiment, a set of two or more adjacent ones of R 21 to R 28 do not bond to each other.
In compound M3 according to one embodiment, R 21 to R 28 are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group). be.
In compound M3 according to one embodiment, R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted carbazolyl group. It is an unsubstituted dibenzofuranyl group.
In compound M3 according to one embodiment, R 21 to R 28 are hydrogen atoms.
In compound M3 according to one embodiment, at least one of R 21 to R 28 is a deuterium atom.

　一実施形態に係る化合物Ｍ３において、Ｒ１１～Ｒ２０のうちの隣接する２つ以上からなる組が互いに結合しない。
　一実施形態に係る化合物Ｍ３において、Ｒ１１～Ｒ２０は、それぞれ独立に、水素原子、置換もしくは無置換の環形成炭素数６～３０のアリール基（好ましくは置換もしくは無置換のフェニル基）である。
　一実施形態に係る化合物Ｍ３において、Ｒ１１～Ｒ２０は、それぞれ独立に、水素原子、置換もしくは無置換のフェニル基、置換もしくは無置換のビフェニル基、又は置換もしくは無置換のカルバゾリル基である。
　一実施形態に係る化合物Ｍ３において、Ｒ１１～Ｒ２０は水素原子である。
　一実施形態に係る化合物Ｍ３において、Ｒ１１～Ｒ２０の少なくとも１つは重水素原子である。 In compound M3 according to one embodiment, a set of two or more adjacent ones of R 11 to R 20 do not bond to each other.
In compound M3 according to one embodiment, R 11 to R 20 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group). be.
In compound M3 according to one embodiment, R 11 to R 20 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted carbazolyl group.
In compound M3 according to one embodiment, R 11 to R 20 are hydrogen atoms.
In compound M3 according to one embodiment, at least one of R 11 to R 20 is a deuterium atom.

　一実施形態に係る化合物Ｍ３において、Ｒ１００は、それぞれ独立に、水素原子、又は置換もしくは無置換の環形成炭素数６～３０のアリール基（好ましくは置換もしくは無置換のフェニル基）である。
　一実施形態に係る化合物Ｍ３において、Ｒ１００は、それぞれ独立に、水素原子、置換もしくは無置換のフェニル基、置換もしくは無置換のビフェニル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のカルバゾリル基、置換もしくは無置換の炭素数１～６のアルキル基、又はトリメチルシリル基である。
　一実施形態に係る化合物Ｍ３において、Ｒ１００は水素原子である。
　一実施形態に係る化合物Ｍ３において、複数のＲ１００のうち、少なくとも１つは重水素原子である。 In compound M3 according to one embodiment, R 100 is each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).
In compound M3 according to one embodiment, R 100 each independently represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzofuranyl group. carbazolyl group, substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or trimethylsilyl group.
In compound M3 according to one embodiment, R 100 is a hydrogen atom.
In compound M3 according to one embodiment, at least one of the plurality of R 100 is a deuterium atom.

　一実施形態に係る化合物Ｍ３において、Ｒ１００は、－Ｎ（Ｒｚ）２で表される基ではない。
　一実施形態に係る化合物Ｍ３は、
　前記一般式（１００－１）～（１００－３）で表される化合物、及び
　前記一般式（１００－４Ａ）～（１００－４Ｄ）で表される化合物からなる群から選択されるいずれかの化合物である。ただし、前記一般式（１００－４Ａ）～（１００－４Ｄ）中、Ｒ１００は、－Ｎ（Ｒｚ）２で表される基ではないことが好ましい。
　前記一般式（１００－１）～（１００－３）で表される化合物は、第四実施形態に係る化合物のうち、一般式（１００－１）～（１００－３）で表される化合物と同義である。
　前記一般式（１００－４Ａ）～（１００－４Ｄ）で表され、かつＲ１００が、－Ｎ（Ｒｚ）２で表される基ではない化合物は、第四実施形態に係る化合物のうち、一般式（１００－４）で表される化合物と同義である。 In compound M3 according to one embodiment, R 100 is not a group represented by -N(Rz) 2 .
Compound M3 according to one embodiment is
Any one selected from the group consisting of compounds represented by the general formulas (100-1) to (100-3), and compounds represented by the general formulas (100-4A) to (100-4D). It is a compound. However, in the general formulas (100-4A) to (100-4D), R 100 is preferably not a group represented by -N(Rz) 2 .
The compounds represented by the general formulas (100-1) to (100-3) are the same as the compounds represented by the general formulas (100-1) to (100-3) among the compounds according to the fourth embodiment. are synonymous.
The compounds represented by the general formulas (100-4A) to (100-4D) and in which R 100 is not a group represented by -N(Rz) 2 are the general formulas among the compounds according to the fourth embodiment. It has the same meaning as the compound represented by formula (100-4).

　一実施形態に係る発光層において、遅延蛍光性の化合物Ｍ２の一重項エネルギーＳ１（Ｍ２）よりも大きい一重項エネルギーＳ１を有する化合物は、化合物Ｍ３のみである。 In the light emitting layer according to one embodiment, compound M3 is the only compound having singlet energy S 1 larger than singlet energy S 1 (M2) of delayed fluorescent compound M2.

・本実施形態の化合物Ｍ３の製造方法
　本実施形態の化合物Ｍ３は、例えば、後述する実施例に記載の方法により製造することができる。本実施形態の化合物Ｍ３は、後述する実施例で説明する反応に倣い、目的物に合わせた既知の代替反応や原料を用いることで、製造することができる。 - Method for producing compound M3 of the present embodiment Compound M3 of the present embodiment can be produced, for example, by the method described in Examples described below. Compound M3 of the present embodiment can be produced by following the reactions described in the examples below and using known alternative reactions and raw materials that match the target product.

　本実施形態の化合物Ｍ３の具体例としては、例えば、以下の化合物が挙げられる。ただし、本発明は、これら化合物の具体例に限定されない。 Specific examples of the compound M3 of this embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.

（化合物Ｍ２）
　本実施形態の発光層は、遅延蛍光性の化合物Ｍ２を含む。 (Compound M2)
The light-emitting layer of this embodiment includes a delayed fluorescent compound M2.

・遅延蛍光性
　遅延蛍光については、「有機半導体のデバイス物性」（安達千波矢編、講談社発行）の２６１～２６８ページで解説されている。その文献の中で、蛍光発光材料の励起一重項状態と励起三重項状態のエネルギー差ΔＥ１３を小さくすることができれば、通常は遷移確率が低い励起三重項状態から励起一重項状態への逆エネルギー移動が高効率で生じ、熱活性化遅延蛍光（Ｔｈｅｒｍａｌｌｙ　Ａｃｔｉｖａｔｅｄ ｄｅｌａｙｅｄ　Ｆｌｕｏｒｅｓｃｅｎｃｅ， ＴＡＤＦ）が発現すると説明されている。さらに、当該文献中の図１０．３８で、遅延蛍光の発生メカニズムが説明されている。本実施形態における化合物Ｍ２は、このようなメカニズムで発生する熱活性化遅延蛍光を示す化合物であることが好ましい。 - Delayed fluorescence Delayed fluorescence is explained on pages 261 to 268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). In that literature, it is stated that if the energy difference ΔE 13 between the excited singlet state and excited triplet state of a fluorescent material can be reduced, the reverse energy from the excited triplet state to the excited singlet state, which normally has a low transition probability, can be reduced. It is explained that the transfer occurs with high efficiency and that thermally activated delayed fluorescence (TADF) is expressed. Furthermore, in Figure 10.38 of the document, the mechanism of generation of delayed fluorescence is explained. Compound M2 in this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

　一般に、遅延蛍光の発光は過渡ＰＬ（Ｐｈｏｔｏ　Ｌｕｍｉｎｅｓｃｅｎｃｅ）測定により確認できる。 In general, delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.

　過渡ＰＬ測定から得た減衰曲線に基づいて遅延蛍光の挙動を解析することもできる。過渡ＰＬ測定とは、試料にパルスレーザーを照射して励起させ、照射を止めた後のＰＬ発光の減衰挙動（過渡特性）を測定する手法である。ＴＡＤＦ材料におけるＰＬ発光は、最初のＰＬ励起で生成する一重項励起子からの発光成分と、三重項励起子を経由して生成する一重項励起子からの発光成分に分類される。最初のＰＬ励起で生成する一重項励起子の寿命は、ナノ秒オーダーであり、非常に短い。そのため、当該一重項励起子からの発光は、パルスレーザーを照射後、速やかに減衰する。
　一方、遅延蛍光は、寿命の長い三重項励起子を経由して生成する一重項励起子からの発光のため、ゆるやかに減衰する。このように最初のＰＬ励起で生成する一重項励起子からの発光と、三重項励起子を経由して生成する一重項励起子からの発光とでは、時間的に大きな差がある。そのため、遅延蛍光由来の発光強度を求めることができる。 The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurement is a method of irradiating a sample with a pulsed laser to excite it, and measuring the attenuation behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission in a TADF material is classified into an emission component from singlet excitons generated by initial PL excitation and an emission component from singlet excitons generated via triplet excitons. The lifetime of the singlet exciton generated by the first PL excitation is on the order of nanoseconds, which is very short. Therefore, the light emission from the singlet exciton attenuates quickly after irradiation with the pulsed laser.
On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons that are generated via long-lived triplet excitons. As described above, there is a large temporal difference between the light emission from singlet excitons generated by the initial PL excitation and the light emission from singlet excitons generated via triplet excitons. Therefore, the luminescence intensity derived from delayed fluorescence can be determined.

　図２には、過渡ＰＬを測定するための例示的装置の概略図が示されている。図２を用いた過渡ＰＬの測定方法、および遅延蛍光の挙動解析の一例を説明する。 A schematic diagram of an exemplary apparatus for measuring transient PL is shown in FIG. An example of a method for measuring transient PL and behavior analysis of delayed fluorescence using FIG. 2 will be described.

　図２の過渡ＰＬ測定装置１００は、所定波長の光を照射可能なパルスレーザー部１０１と、測定試料を収容する試料室１０２と、測定試料から放射された光を分光する分光器１０３と、２次元像を結像するためのストリークカメラ１０４と、２次元像を取り込んで解析するパーソナルコンピュータ１０５とを備える。なお、過渡ＰＬの測定は、図２に記載の装置に限定されない。 The transient PL measurement device 100 in FIG. 2 includes a pulse laser section 101 capable of emitting light of a predetermined wavelength, a sample chamber 102 that accommodates a measurement sample, a spectrometer 103 that spectrally spectra the light emitted from the measurement sample, and 2. It includes a streak camera 104 for forming dimensional images, and a personal computer 105 for capturing and analyzing two-dimensional images. Note that the measurement of transient PL is not limited to the apparatus shown in FIG. 2.

　試料室１０２に収容される試料は、マトリックス材料に対し、ドーピング材料が１２質量％の濃度でドープされた薄膜を石英基板に成膜することで得られる。 The sample accommodated in the sample chamber 102 is obtained by forming a thin film doped with a doping material at a concentration of 12% by mass relative to the matrix material on a quartz substrate.

　試料室１０２に収容された薄膜試料に対し、パルスレーザー部１０１からパルスレーザーを照射してドーピング材料を励起させる。励起光の照射方向に対して９０度の方向へ発光を取り出し、取り出した光を分光器１０３で分光し、ストリークカメラ１０４内で２次元像を結像する。その結果、縦軸が時間に対応し、横軸が波長に対応し、輝点が発光強度に対応する２次元画像を得ることができる。この２次元画像を所定の時間軸で切り出すと、縦軸が発光強度であり、横軸が波長である発光スペクトルを得ることができる。また、当該２次元画像を波長軸で切り出すと、縦軸が発光強度の対数であり、横軸が時間である減衰曲線（過渡ＰＬ）を得ることができる。 The thin film sample housed in the sample chamber 102 is irradiated with a pulsed laser from the pulsed laser section 101 to excite the doping material. Emitted light is extracted in a direction 90 degrees with respect to the irradiation direction of the excitation light, the extracted light is separated into spectra by a spectroscope 103, and a two-dimensional image is formed within a streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spots correspond to emission intensity. By cutting out this two-dimensional image along a predetermined time axis, it is possible to obtain an emission spectrum in which the vertical axis is the emission intensity and the horizontal axis is the wavelength. Moreover, when the two-dimensional image is cut out along the wavelength axis, an attenuation curve (transient PL) can be obtained in which the vertical axis is the logarithm of the emission intensity and the horizontal axis is the time.

　例えば、マトリックス材料として、下記参考化合物Ｈ１を用い、ドーピング材料として下記参考化合物Ｄ１を用いて上述のようにして薄膜試料Ａを作製し、過渡ＰＬ測定を行った。 For example, a thin film sample A was prepared as described above using reference compound H1 below as a matrix material and reference compound D1 below as a doping material, and transient PL measurement was performed.

　ここでは、前述の薄膜試料Ａ、および薄膜試料Ｂを用いて減衰曲線を解析した。薄膜試料Ｂは、マトリックス材料として下記参考化合物Ｈ２を用い、ドーピング材料として前記参考化合物Ｄ１を用いて、上述のようにして薄膜試料を作製した。 Here, the attenuation curves were analyzed using the aforementioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the following reference compound H2 as the matrix material and the reference compound D1 as the doping material.

　図３には、薄膜試料Ａおよび薄膜試料Ｂについて測定した過渡ＰＬから得た減衰曲線が示されている。 FIG. 3 shows attenuation curves obtained from the transient PL measured for thin film sample A and thin film sample B.

　上記したように過渡ＰＬ測定によって、縦軸を発光強度とし、横軸を時間とする発光減衰曲線を得ることができる。この発光減衰曲線に基づいて、光励起により生成した一重項励起状態から発光する蛍光と、三重項励起状態を経由し、逆エネルギー移動により生成する一重項励起状態から発光する遅延蛍光との、蛍光強度比を見積もることができる。遅延蛍光性の材料では、素早く減衰する蛍光の強度に対し、緩やかに減衰する遅延蛍光の強度の割合が、ある程度大きい。 As described above, by transient PL measurement, it is possible to obtain a luminescence attenuation curve with the vertical axis representing the luminous intensity and the horizontal axis representing time. Based on this emission decay curve, the fluorescence intensity of the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state is determined. The ratio can be estimated. In materials with delayed fluorescence, the ratio of the intensity of delayed fluorescence that decays slowly to the intensity of fluorescence that decays quickly is relatively large.

　具体的には、遅延蛍光性の材料からの発光としては、Ｐｒｏｍｐｔ発光（即時発光）と、Ｄｅｌａｙ発光（遅延発光）とが存在する。Ｐｒｏｍｐｔ発光（即時発光）とは、当該遅延蛍光性の材料が吸収する波長のパルス光（パルスレーザーから照射される光）で励起された後、当該励起状態から即座に観察される発光である。Ｄｅｌａｙ発光（遅延発光）とは、当該パルス光による励起後、即座には観察されず、その後観察される発光である。 Specifically, there are two types of light emission from a delayed fluorescent material: prompt light emission (immediate light emission) and delayed light emission (delayed light emission). Prompt light emission (immediate light emission) is light emission that is observed immediately from the excited state after being excited by pulsed light (light emitted from a pulsed laser) at a wavelength that the delayed fluorescent material absorbs. Delayed light emission is light emission that is not observed immediately after excitation by the pulsed light but is observed afterward.

　Ｐｒｏｍｐｔ発光とＤｅｌａｙ発光の量とその比は、“Ｎａｔｕｒｅ　４９２，　２３４－２３８，　２０１２”（参考文献１）に記載された方法と同様の方法により求めることができる。なお、Ｐｒｏｍｐｔ発光とＤｅｌａｙ発光の量の算出に使用される装置は、前記参考文献１に記載の装置、または図２に記載の装置に限定されない。 The amount of prompt light emission and delay light emission and the ratio thereof can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference Document 1). Note that the device used to calculate the amount of prompt light emission and delay light emission is not limited to the device described in reference document 1 or the device described in FIG. 2.

　また、本明細書では、化合物Ｍ２の遅延蛍光性の測定には、次に示す方法により作製した試料を用いる。例えば、化合物Ｍ２をトルエンに溶解し、自己吸収の寄与を取り除くため励起波長において吸光度が０．０５以下の希薄溶液を調製する。また酸素による消光を防ぐため、試料溶液を凍結脱気した後にアルゴン雰囲気下で蓋付きのセルに封入することで、アルゴンで飽和された酸素フリーの試料溶液とする。
　上記試料溶液の蛍光スペクトルを分光蛍光光度計ＦＰ－８６００（日本分光社製）で測定し、また同条件で９，１０－ジフェニルアントラセンのエタノール溶液の蛍光スペクトルを測定する。両スペクトルの蛍光面積強度を用いて、Ｍｏｒｒｉｓ　ｅｔ　ａｌ．　Ｊ．Ｐｈｙｓ．Ｃｈｅｍ．８０（１９７６）９６９中の（１）式により全蛍光量子収率を算出する。 Furthermore, in this specification, a sample prepared by the following method is used to measure the delayed fluorescence of compound M2. For example, compound M2 is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption. Furthermore, in order to prevent quenching due to oxygen, the sample solution is frozen and degassed and then sealed in a cell with a lid under an argon atmosphere, thereby making the sample solution saturated with argon and oxygen-free.
The fluorescence spectrum of the above sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. Using the fluorescence area intensity of both spectra, Morris et al. J. Phys. Chem. The total fluorescence quantum yield is calculated using equation (1) in 80 (1976) 969.

　本実施形態においては、測定対象化合物（化合物Ｍ２）のＰｒｏｍｐｔ発光（即時発光）の量をＸＰとし、Ｄｅｌａｙ発光（遅延発光）の量をＸＤとしたときに、ＸＤ／ＸＰの値が０．０５以上であることが好ましい。
　本明細書における化合物Ｍ２以外の化合物のＰｒｏｍｐｔ発光とＤｅｌａｙ発光の量とその比の測定も、化合物Ｍ２のＰｒｏｍｐｔ発光とＤｅｌａｙ発光の量とその比の測定と同様である。 In this embodiment, when the amount of prompt light emission (immediate light emission) of the compound to be measured (compound M2 ) is represented by is preferably 0.05 or more.
In this specification, the measurement of the amount of prompt emission and delay emission and the ratio thereof of compounds other than compound M2 is also the same as the measurement of the amount of prompt emission and delay emission of compound M2 and the ratio thereof.

・本実施形態の化合物Ｍ２の製造方法
　本実施形態の化合物Ｍ２は、公知の方法により製造することができる。 - Manufacturing method of compound M2 of this embodiment Compound M2 of this embodiment can be manufactured by a known method.

　本実施形態の化合物Ｍ２の具体例としては、例えば、以下の化合物が挙げられる。ただし、本発明は、これら化合物の具体例に限定されない。 Specific examples of the compound M2 of this embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.

＜発光層における化合物Ｍ３及び化合物Ｍ２の関係＞
　本実施形態の有機ＥＬ素子において、化合物Ｍ２の一重項エネルギーＳ１（Ｍ２）と、化合物Ｍ３の一重項エネルギーＳ１（Ｍ３）とは、下記数式（数１）の関係を満たす。
　　　Ｓ１（Ｍ３）＞Ｓ１（Ｍ２）　　　（数１） <Relationship between compound M3 and compound M2 in the light emitting layer>
In the organic EL device of this embodiment, the singlet energy S 1 (M2) of the compound M2 and the singlet energy S 1 (M3) of the compound M3 satisfy the relationship of the following formula (Equation 1).
S 1 (M3)>S 1 (M2) (Math. 1)

　化合物Ｍ３の７７［Ｋ］におけるエネルギーギャップＴ７７Ｋ（Ｍ３）は、化合物Ｍ２の７７［Ｋ］におけるエネルギーギャップＴ７７Ｋ（Ｍ２）よりも大きいことが好ましい。すなわち、下記数式（数１１）の関係を満たすことが好ましい。
　　　Ｔ７７Ｋ（Ｍ３）＞Ｔ７７Ｋ（Ｍ２）　　　…（数１１） The energy gap T 77K (M3) of compound M3 at 77 [K] is preferably larger than the energy gap T 77K (M2) of compound M2 at 77 [K]. That is, it is preferable that the relationship of the following mathematical formula (Equation 11) be satisfied.
T 77K (M3)>T 77K (M2) ... (Math. 11)

　本実施形態の有機ＥＬ素子を発光させたときに、発光層において、化合物Ｍ３が主に発光していないことが好ましい。 When the organic EL element of this embodiment emits light, it is preferable that compound M3 does not primarily emit light in the light emitting layer.

・三重項エネルギーと７７［Ｋ］におけるエネルギーギャップとの関係
　ここで、三重項エネルギーと７７［Ｋ］におけるエネルギーギャップとの関係について説明する。本実施形態では、７７［Ｋ］におけるエネルギーギャップは、通常定義される三重項エネルギーとは異なる点がある。
　三重項エネルギーの測定は、次のようにして行われる。まず、測定対象となる化合物を適切な溶媒中に溶解した溶液を石英ガラス管内に封入した試料を作製する。この試料について、低温（７７［Ｋ］）で燐光スペクトル（縦軸：燐光発光強度、横軸：波長とする。）を測定し、この燐光スペクトルの短波長側の立ち上がりに対して接線を引き、その接線と横軸との交点の波長値に基づいて、所定の換算式から三重項エネルギーを算出する。
　ここで、本実施形態に係る化合物の内、熱活性遅延蛍光性の化合物は、ΔＳＴが小さい化合物であることが好ましい。ΔＳＴが小さいと、低温（７７［Ｋ］）状態でも、項間交差、及び逆項間交差が起こりやすく、励起一重項状態と励起三重項状態とが混在する。その結果、上記と同様にして測定されるスペクトルは、励起一重項状態、及び励起三重項状態の両者からの発光を含んでおり、いずれの状態から発光したのかについて峻別することは困難であるが、基本的には三重項エネルギーの値が支配的と考えられる。
　そのため、本実施形態では、通常の三重項エネルギーＴと測定手法は同じであるが、その厳密な意味において異なることを区別するため、次のようにして測定される値をエネルギーギャップＴ７７Ｋと称する。測定対象となる化合物をＥＰＡ（ジエチルエーテル：イソペンタン：エタノール＝５：５：２（容積比））中に、濃度が１０μｍｏｌ／Ｌとなるように溶解し、この溶液を石英セル中に入れて測定試料とする。この測定試料について、低温（７７［Ｋ］）で燐光スペクトル（縦軸：燐光発光強度、横軸：波長とする。）を測定し、この燐光スペクトルの短波長側の立ち上がりに対して接線を引き、その接線と横軸との交点の波長値λｅｄｇｅ［ｎｍ］に基づいて、次の換算式（Ｆ１）から算出されるエネルギー量を７７［Ｋ］におけるエネルギーギャップＴ７７Ｋとする。
　　換算式（Ｆ１）：Ｔ７７Ｋ［ｅＶ］＝１２３９．８５／λｅｄｇｅ -Relationship between triplet energy and energy gap at 77[K] Here, the relationship between triplet energy and the energy gap at 77[K] will be explained. In this embodiment, the energy gap at 77 [K] differs from the normally defined triplet energy.
Triplet energy is measured as follows. First, a sample is prepared by sealing a solution in which a compound to be measured is dissolved in an appropriate solvent in a quartz glass tube. For this sample, measure the phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) at low temperature (77 [K]), draw a tangent to the rise of the short wavelength side of this phosphorescence spectrum, Triplet energy is calculated from a predetermined conversion formula based on the wavelength value at the intersection of the tangent and the horizontal axis.
Here, among the compounds according to this embodiment, the heat-activated delayed fluorescent compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even in a low temperature (77 [K]) state, and excited singlet states and excited triplet states coexist. As a result, the spectrum measured in the same manner as above includes light emission from both the excited singlet state and the excited triplet state, and it is difficult to clearly distinguish from which state the light is emitted. , basically the value of triplet energy is considered to be dominant.
Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish that they are different in the strict sense, the value measured as follows is referred to as the energy gap T 77K . . The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol/L, and this solution is placed in a quartz cell for measurement. Use as a sample. For this measurement sample, measure the phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) at a low temperature (77 [K]), and draw a tangent to the rise of the short wavelength side of this phosphorescence spectrum. , the energy amount calculated from the following conversion formula (F1) based on the wavelength value λ edge [nm] at the intersection of the tangent and the horizontal axis is defined as the energy gap T 77K at 77 [K].
Conversion formula (F1): T 77K [eV] = 1239.85/λ edge

　燐光スペクトルの短波長側の立ち上がりに対する接線は以下のように引く。燐光スペクトルの短波長側から、スペクトルの極大値のうち、最も短波長側の極大値までスペクトル曲線上を移動する際に、長波長側に向けて曲線上の各点における接線を考える。この接線は、曲線が立ち上がるにつれ（つまり縦軸が増加するにつれ）、傾きが増加する。この傾きの値が極大値をとる点において引いた接線（すなわち変曲点における接線）が、当該燐光スペクトルの短波長側の立ち上がりに対する接線とする。
　なお、スペクトルの最大ピーク強度の１５％以下のピーク強度をもつ極大点は、上述の最も短波長側の極大値には含めず、最も短波長側の極大値に最も近い、傾きの値が極大値をとる点において引いた接線を当該燐光スペクトルの短波長側の立ち上がりに対する接線とする。
　燐光の測定には、（株）日立ハイテクノロジー製のＦ－４５００形分光蛍光光度計本体を用いることができる。なお、測定装置はこの限りではなく、冷却装置、及び低温用容器と、励起光源と、受光装置とを組み合わせることにより、測定してもよい。 The tangent to the rise of the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values of the spectrum, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent line increases as the curve rises (ie, as the vertical axis increases). The tangent drawn at the point where the value of this slope takes the maximum value (that is, the tangent at the inflection point) is the tangent to the rise of the short wavelength side of the phosphorescence spectrum.
Note that a local maximum point with a peak intensity that is 15% or less of the maximum peak intensity of the spectrum is not included in the local maximum value on the shortest wavelength side mentioned above, but is included in the maximum value of the slope that is closest to the local maximum value on the shortest wavelength side. The tangent line drawn at the point where the value is taken is the tangent line to the rise of the short wavelength side of the phosphorescence spectrum.
For the measurement of phosphorescence, an F-4500 spectrofluorometer manufactured by Hitachi High-Technologies Corporation can be used. Note that the measurement device is not limited to this, and measurement may be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

・一重項エネルギーＳ１
　溶液を用いた一重項エネルギーＳ１の測定方法（溶液法と称する場合がある。）としては、下記の方法が挙げられる。
　測定対象となる化合物の１０μｍｏｌ／Ｌトルエン溶液を調製して石英セルに入れ、常温（３００Ｋ）でこの試料の吸収スペクトル（縦軸：吸収強度、横軸：波長とする。）を測定する。この吸収スペクトルの長波長側の立ち下がりに対して接線を引き、その接線と横軸との交点の波長値λｅｄｇｅ［ｎｍ］を次に示す換算式（Ｆ２）に代入して一重項エネルギーを算出する。
　　換算式（Ｆ２）：Ｓ１［ｅＶ］＝１２３９．８５／λｅｄｇｅ
　吸収スペクトル測定装置としては、例えば、日立社製の分光光度計（装置名：Ｕ３３１０）が挙げられるが、これに限定されない。 ・Singlet energy S 1
Examples of the method for measuring singlet energy S1 using a solution (sometimes referred to as a solution method) include the following method.
A 10 μmol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300K). Draw a tangent to the falling edge of the long wavelength side of this absorption spectrum, and calculate the singlet energy by substituting the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis into the conversion formula (F2) shown below. do.
Conversion formula (F2): S 1 [eV] = 1239.85/λedge
Examples of the absorption spectrum measuring device include, but are not limited to, a spectrophotometer manufactured by Hitachi (device name: U3310).

　吸収スペクトルの長波長側の立ち下がりに対する接線は以下のように引く。吸収スペクトルの極大値のうち、最も長波長側の極大値から長波長方向にスペクトル曲線上を移動する際に、曲線上の各点における接線を考える。この接線は、曲線が立ち下がるにつれ（つまり縦軸の値が減少するにつれ）、傾きが減少しその後増加することを繰り返す。傾きの値が最も長波長側（ただし、吸光度が０．１以下となる場合は除く）で極小値をとる点において引いた接線を当該吸収スペクトルの長波長側の立ち下がりに対する接線とする。
　なお、吸光度の値が０．２以下の極大点は、上記最も長波長側の極大値には含めない。 The tangent to the falling edge of the long wavelength side of the absorption spectrum is drawn as follows. When moving on a spectrum curve in the long wavelength direction from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum, consider tangents at each point on the curve. The slope of this tangent line repeats decreasing and then increasing as the curve falls (that is, as the value on the vertical axis decreases). The tangent line drawn at the point where the slope value takes the minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is the tangent to the fall of the long wavelength side of the absorption spectrum.
Note that a maximum point with an absorbance value of 0.2 or less is not included in the maximum value on the longest wavelength side.

　本実施形態では、一重項エネルギーＳ１と、７７［Ｋ］におけるエネルギーギャップＴ７７Ｋとの差（Ｓ１－Ｔ７７Ｋ）をΔＳＴとして定義する。 In this embodiment, the difference (S 1 −T 77K ) between the singlet energy S 1 and the energy gap T 77K at 77 [K] is defined as ΔST.

　本実施形態において、化合物Ｍ２の一重項エネルギーＳ１（Ｍ２）と、化合物Ｍ２の７７［Ｋ］におけるエネルギーギャップＴ７７Ｋ（Ｍ２）との差ΔＳＴ（Ｍ２）は、好ましくは０．３ｅＶ未満、より好ましくは０．２ｅＶ未満、さらに好ましくは０．１ｅＶ未満、よりさらに好ましくは０．０１ｅＶ未満である。すなわち、ΔＳＴ（Ｍ２）は、下記数式（数１Ａ）～（数１Ｄ）のいずれかの関係を満たすことが好ましい。
ΔＳＴ（Ｍ２）＝Ｓ１（Ｍ２）－Ｔ７７Ｋ（Ｍ２）＜０．３ｅＶ（数１Ａ）
ΔＳＴ（Ｍ２）＝Ｓ１（Ｍ２）－Ｔ７７Ｋ（Ｍ２）＜０．２ｅＶ（数１Ｂ）
ΔＳＴ（Ｍ２）＝Ｓ１（Ｍ２）－Ｔ７７Ｋ（Ｍ２）＜０．１ｅＶ（数１Ｃ）
ΔＳＴ（Ｍ２）＝Ｓ１（Ｍ２）－Ｔ７７Ｋ（Ｍ２）＜０．０１ｅＶ（数１Ｄ） In this embodiment, the difference ΔST(M2) between the singlet energy S 1 (M2) of the compound M2 and the energy gap T 77K (M2) at 77[K] of the compound M2 is preferably less than 0.3 eV, more preferably Preferably it is less than 0.2 eV, more preferably less than 0.1 eV, even more preferably less than 0.01 eV. That is, it is preferable that ΔST(M2) satisfy any one of the following mathematical expressions (Equation 1A) to (Equation 1D).
ΔST(M2)=S 1 (M2)-T 77K (M2)<0.3eV (Several 1A)
ΔST(M2)=S 1 (M2)-T 77K (M2)<0.2eV (Math. 1B)
ΔST (M2) = S 1 (M2) - T 77K (M2) < 0.1eV (Several 1C)
ΔST (M2) = S 1 (M2) - T 77K (M2) < 0.01 eV (Math. 1D)

・発光層の膜厚
　本実施形態に係る有機ＥＬ素子における発光層の膜厚は、好ましくは５ｎｍ以上５０ｎｍ以下、より好ましくは７ｎｍ以上５０ｎｍ以下、最も好ましくは１０ｎｍ以上５０ｎｍ以下である。５ｎｍ以上であると、発光層形成及び色度の調整が容易になりやすく、５０ｎｍ以下であると、駆動電圧の上昇が抑制されやすい。 - Thickness of the light-emitting layer The thickness of the light-emitting layer in the organic EL element according to this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and most preferably 10 nm or more and 50 nm or less. When the thickness is 5 nm or more, it is easy to form a light emitting layer and adjust the chromaticity, and when it is 50 nm or less, an increase in driving voltage is easily suppressed.

・発光層における化合物の含有率
　発光層に含まれている化合物Ｍ２及び化合物Ｍ３の含有率は、例えば、以下の範囲であることが好ましい。
　化合物Ｍ２の含有率は、１０質量％以上８０質量％以下であることが好ましく、１０質量％以上６０質量％以下であることがより好ましく、２０質量％以上６０質量％以下であることがさらに好ましい。
　化合物Ｍ３の含有率は、２０質量％以上９０質量％以下であることが好ましく、４０質量％以上９０質量％以下であることがより好ましく、４０質量％以上８０質量％以下であることがさらに好ましい。
　なお、本実施形態は、発光層に、化合物Ｍ２及び化合物Ｍ３以外の材料が含まれることを除外しない。
　発光層は、化合物Ｍ２を１種のみ含んでもよいし、２種以上含んでもよい。発光層は、化合物Ｍ３を１種のみ含んでもよいし、２種以上含んでもよい。 - Content rate of compound in the light emitting layer The content rate of the compound M2 and the compound M3 contained in the light emitting layer is preferably in the following range, for example.
The content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. .
The content of compound M3 is preferably 20% by mass or more and 90% by mass or less, more preferably 40% by mass or more and 90% by mass or less, and even more preferably 40% by mass or more and 80% by mass or less. .
Note that this embodiment does not exclude that the light-emitting layer includes materials other than compound M2 and compound M3.
The light-emitting layer may contain only one type of compound M2, or may contain two or more types of compound M2. The light-emitting layer may contain only one type of compound M3, or may contain two or more types of compound M3.

　図４は、発光層における化合物Ｍ３及び化合物Ｍ２のエネルギー準位の関係の一例を示す図である。図４において、Ｓ０は、基底状態を表す。Ｓ１（Ｍ２）は、化合物Ｍ２の最低励起一重項状態を表し、Ｔ１（Ｍ２）は、化合物Ｍ２の最低励起三重項状態を表す。Ｓ１（Ｍ３）は、化合物Ｍ３の最低励起一重項状態を表し、Ｔ１（Ｍ３）は、化合物Ｍ３の最低励起三重項状態を表す。図４に示すように、化合物Ｍ２としてΔＳＴ（Ｍ２）の小さな材料を用いると、化合物Ｍ２の最低励起三重項状態Ｔ１は熱エネルギーによって最低励起一重項状態Ｓ１に逆項間交差することが可能である。
　この化合物Ｍ２で生じる逆項間交差を利用することで、発光層が、化合物Ｍ２の最低励起一重項状態Ｓ１（Ｍ２）よりも小さい最低励起一重項状態Ｓ１の蛍光ドーパントを含まない場合は、化合物Ｍ２の最低励起一重項状態Ｓ１（Ｍ２）からの発光を観測することができる。このＴＡＤＦ機構による遅延蛍光を利用することによっても、理論的に内部量子効率を１００％まで高めることができると考えられている。 FIG. 4 is a diagram showing an example of the relationship between the energy levels of compound M3 and compound M2 in the light emitting layer. In FIG. 4, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. As shown in FIG. 4, when a material with small ΔST(M2) is used as compound M2, the lowest excited triplet state T1 of compound M2 can reverse intersystem cross to the lowest excited singlet state S1 by thermal energy. be.
By utilizing the reverse intersystem crossing that occurs in compound M2, if the light-emitting layer does not contain a fluorescent dopant in the lowest excited singlet state S1 (M2), which is smaller than the lowest excited singlet state S1 (M2) of compound M2, the compound Emission from the lowest excited singlet state S1 (M2) of M2 can be observed. It is believed that the internal quantum efficiency can be theoretically increased to 100% by utilizing delayed fluorescence caused by this TADF mechanism.

　本実施形態の有機ＥＬ素子は、発光層に、遅延蛍光性の化合物Ｍ２と、前記化合物Ｍ２よりも大きな一重項エネルギーを有する化合物Ｍ３（前記一般式（１－１）または（１－２）で表される化合物Ｍ３）とを含んでいる。
　本実施形態によれば、高性能な有機ＥＬ素子が実現される。
　本実施形態の一態様によれば、高効率で発光する有機ＥＬ素子が実現される。
　本実施形態の一態様によれば、長寿命で発光する有機ＥＬ素子が実現される。
　本実施形態の有機ＥＬ素子は、表示装置および発光装置等の電子機器に使用できる。 The organic EL device of this embodiment includes a delayed fluorescent compound M2 and a compound M3 (formula (1-1) or (1-2)) having a larger singlet energy than the compound M2 in the light emitting layer. It contains the represented compound M3).
According to this embodiment, a high-performance organic EL element is realized.
According to one aspect of this embodiment, an organic EL element that emits light with high efficiency is realized.
According to one aspect of this embodiment, an organic EL element that emits light with a long life is realized.
The organic EL element of this embodiment can be used in electronic devices such as display devices and light emitting devices.

　有機ＥＬ素子の構成についてさらに説明する。 The structure of the organic EL element will be further explained.

（基板）
　基板は、有機ＥＬ素子の支持体として用いられる。基板としては、例えば、ガラス、石英、及びプラスチック等を用いることができる。また、可撓性基板を用いてもよい。可撓性基板とは、折り曲げることができる（フレキシブル）基板のことであり、例えば、プラスチック基板等が挙げられる。プラスチック基板を形成する材料としては、例えば、ポリカーボネート、ポリアリレート、ポリエーテルスルフォン、ポリプロピレン、ポリエステル、ポリフッ化ビニル、ポリ塩化ビニル、ポリイミド、及びポリエチレンナフタレート等が挙げられる。また、無機蒸着フィルムを用いることもできる。 (substrate)
The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, plastic, etc. can be used. Alternatively, a flexible substrate may be used. The flexible substrate refers to a (flexible) substrate that can be bent, and includes, for example, a plastic substrate. Examples of materials forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Moreover, an inorganic vapor-deposited film can also be used.

（陽極）
　基板上に形成される陽極には、仕事関数の大きい（具体的には４．０ｅＶ以上）金属、合金、電気伝導性化合物、およびこれらの混合物などを用いることが好ましい。具体的には、例えば、酸化インジウム－酸化スズ（ＩＴＯ：Ｉｎｄｉｕｍ　Ｔｉｎ　Ｏｘｉｄｅ）、珪素もしくは酸化珪素を含有した酸化インジウム－酸化スズ、酸化インジウム－酸化亜鉛、酸化タングステン、および酸化亜鉛を含有した酸化インジウム、グラフェン等が挙げられる。この他、金（Ａｕ）、白金（Ｐｔ）、ニッケル（Ｎｉ）、タングステン（Ｗ）、クロム（Ｃｒ）、モリブデン（Ｍｏ）、鉄（Ｆｅ）、コバルト（Ｃｏ）、銅（Ｃｕ）、パラジウム（Ｐｄ）、チタン（Ｔｉ）、または金属材料の窒化物（例えば、窒化チタン）等が挙げられる。 (anode)
For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. , graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), or a nitride of a metal material (eg, titanium nitride).

　これらの材料は、通常、スパッタリング法により成膜される。例えば、酸化インジウム－酸化亜鉛は、酸化インジウムに対し１質量％以上１０質量％以下の酸化亜鉛を加えたターゲットを用いることにより、スパッタリング法で形成することができる。また、例えば、酸化タングステン、および酸化亜鉛を含有した酸化インジウムは、酸化インジウムに対し酸化タングステンを０．５質量％以上５質量％以下、酸化亜鉛を０．１質量％以上１質量％以下含有したターゲットを用いることにより、スパッタリング法で形成することができる。その他、真空蒸着法、塗布法、インクジェット法、スピンコート法などにより作製してもよい。 These materials are usually deposited using a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target containing 1% by mass or more and 10% by mass or less of zinc oxide relative to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass or more of tungsten oxide and 5% by mass or less, and 0.1% by mass or more and 1% by mass or less of zinc oxide relative to indium oxide. By using a target, it can be formed by a sputtering method. In addition, it may be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, or the like.

　陽極上に形成されるＥＬ層のうち、陽極に接して形成される正孔注入層は、陽極の仕事関数に関係なく正孔（ホール）注入が容易である複合材料を用いて形成されるため、電極材料として可能な材料（例えば、金属、合金、電気伝導性化合物、およびこれらの混合物、その他、元素周期表の第１族または第２族に属する元素も含む）を用いることができる。 Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that allows easy hole injection regardless of the work function of the anode. , materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, mixtures thereof, and other elements belonging to Group 1 or Group 2 of the Periodic Table of Elements) can be used.

　仕事関数の小さい材料である、元素周期表の第１族または第２族に属する元素、すなわちリチウム（Ｌｉ）及びセシウム（Ｃｓ）等のアルカリ金属、マグネシウム（Ｍｇ）、カルシウム（Ｃａ）及びストロンチウム（Ｓｒ）等のアルカリ土類金属、並びにこれらを含む合金（例えば、ＭｇＡｇ、ＡｌＬｉ）、ユーロピウム（Ｅｕ）及びイッテルビウム（Ｙｂ）等の希土類金属並びにこれらを含む合金等を用いることもできる。なお、アルカリ金属、アルカリ土類金属、およびこれらを含む合金を用いて陽極を形成する場合には、真空蒸着法やスパッタリング法を用いることができる。さらに、銀ペーストなどを用いる場合には、塗布法やインクジェット法などを用いることができる。 Elements belonging to Group 1 or Group 2 of the periodic table of elements, which are materials with a small work function, such as alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), calcium (Ca), and strontium ( It is also possible to use alkaline earth metals such as Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. In addition, when forming an anode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when silver paste or the like is used, a coating method, an inkjet method, etc. can be used.

（陰極）
　陰極には、仕事関数の小さい（具体的には３．８ｅＶ以下）金属、合金、電気伝導性化合物、およびこれらの混合物などを用いることが好ましい。このような陰極材料の具体例としては、元素周期表の第１族または第２族に属する元素、すなわちリチウム（Ｌｉ）及びセシウム（Ｃｓ）等のアルカリ金属、マグネシウム（Ｍｇ）、カルシウム（Ｃａ）及びストロンチウム（Ｓｒ）等のアルカリ土類金属、並びにこれらを含む合金（例えば、ＭｇＡｇ、ＡｌＬｉ）、ユーロピウム（Ｅｕ）及びイッテルビウム（Ｙｂ）等の希土類金属並びにこれらを含む合金等が挙げられる。 (cathode)
For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, such as alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), and calcium (Ca). and alkaline earth metals such as strontium (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

　なお、アルカリ金属、アルカリ土類金属、これらを含む合金を用いて陰極を形成する場合には、真空蒸着法やスパッタリング法を用いることができる。また、銀ペーストなどを用いる場合には、塗布法やインクジェット法などを用いることができる。 Note that when forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using silver paste or the like, a coating method, an inkjet method, etc. can be used.

　なお、電子注入層を設けることにより、仕事関数の大小に関わらず、Ａｌ、Ａｇ、ＩＴＯ、グラフェン、珪素もしくは酸化珪素を含有した酸化インジウム－酸化スズ等様々な導電性材料を用いて陰極を形成することができる。これらの導電性材料は、スパッタリング法やインクジェット法、スピンコート法等を用いて成膜することができる。 By providing an electron injection layer, the cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the size of the work function. can do. These conductive materials can be formed into films using a sputtering method, an inkjet method, a spin coating method, or the like.

（正孔注入層）
　正孔注入層は、正孔注入性の高い物質を含む層である。正孔注入性の高い物質としては、モリブデン酸化物、チタン酸化物、バナジウム酸化物、レニウム酸化物、ルテニウム酸化物、クロム酸化物、ジルコニウム酸化物、ハフニウム酸化物、タンタル酸化物、銀酸化物、タングステン酸化物、マンガン酸化物等を用いることができる。 (hole injection layer)
The hole injection layer is a layer containing a substance with high hole injection properties. Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, etc. can be used.

　また、正孔注入性の高い物質としては、低分子の有機化合物である４，４’，４’’－トリス（Ｎ，Ｎ－ジフェニルアミノ）トリフェニルアミン（略称：ＴＤＡＴＡ）、４，４’，４’’－トリス［Ｎ－（３－メチルフェニル）－Ｎ－フェニルアミノ］トリフェニルアミン（略称：ＭＴＤＡＴＡ）、４，４’－ビス［Ｎ－（４－ジフェニルアミノフェニル）－Ｎ－フェニルアミノ］ビフェニル（略称：ＤＰＡＢ）、４，４’－ビス（Ｎ－｛４－［Ｎ’－（３－メチルフェニル）－Ｎ’－フェニルアミノ］フェニル｝－Ｎ－フェニルアミノ）ビフェニル（略称：ＤＮＴＰＤ）、１，３，５－トリス［Ｎ－（４－ジフェニルアミノフェニル）－Ｎ－フェニルアミノ］ベンゼン（略称：ＤＰＡ３Ｂ）、３－［Ｎ－（９－フェニルカルバゾール－３－イル）－Ｎ－フェニルアミノ］－９－フェニルカルバゾール（略称：ＰＣｚＰＣＡ１）、３，６－ビス［Ｎ－（９－フェニルカルバゾール－３－イル）－Ｎ－フェニルアミノ］－９－フェニルカルバゾール（略称：ＰＣｚＰＣＡ２）、３－［Ｎ－（１－ナフチル）－Ｎ－（９－フェニルカルバゾール－３－イル）アミノ］－９－フェニルカルバゾール（略称：ＰＣｚＰＣＮ１）等の芳香族アミン化合物等やジピラジノ［２，３－ｆ：２０，３０－ｈ］キノキサリン－２，３，６，７，１０，１１－ヘキサカルボニトリル（ＨＡＴ－ＣＮ）も挙げられる。 In addition, as substances with high hole injection properties, 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4' , 4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenyl amino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N -phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), Aromatic amine compounds such as 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and dipyrazino[2,3-f :20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

　また、正孔注入性の高い物質としては、高分子化合物（オリゴマー、デンドリマー、ポリマー等）を用いることもできる。例えば、ポリ（Ｎ－ビニルカルバゾール）（略称：ＰＶＫ）、ポリ（４－ビニルトリフェニルアミン）（略称：ＰＶＴＰＡ）、ポリ［Ｎ－（４－｛Ｎ’－［４－（４－ジフェニルアミノ）フェニル］フェニル－Ｎ’－フェニルアミノ｝フェニル）メタクリルアミド］（略称：ＰＴＰＤＭＡ）、ポリ［Ｎ，Ｎ’－ビス（４－ブチルフェニル）－Ｎ，Ｎ’－ビス（フェニル）ベンジジン］（略称：Ｐｏｌｙ－ＴＰＤ）などの高分子化合物が挙げられる。また、ポリ（３，４－エチレンジオキシチオフェン）／ポリ（スチレンスルホン酸）（ＰＥＤＯＴ／ＰＳＳ）、ポリアニリン／ポリ（スチレンスルホン酸）（ＰＡｎｉ／ＰＳＳ）等の酸を添加した高分子化合物を用いることもできる。 Furthermore, as the substance with high hole injection properties, high molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino) phenyl]phenyl-N'-phenylamino}phenyl) methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Polymer compounds such as Poly-TPD) can be mentioned. Additionally, a polymer compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS) or polyaniline/poly(styrene sulfonic acid) (PAni/PSS), is used. You can also do that.

（正孔輸送層）
　正孔輸送層は、正孔輸送性の高い物質を含む層である。正孔輸送層には、芳香族アミン化合物、カルバゾール誘導体、アントラセン誘導体等を使用する事ができる。具体的には、４，４’－ビス［Ｎ－（１－ナフチル）－Ｎ－フェニルアミノ］ビフェニル（略称：ＮＰＢ）やＮ，Ｎ’－ビス（３－メチルフェニル）－Ｎ，Ｎ’－ジフェニル－［１，１’－ビフェニル］－４，４’－ジアミン（略称：ＴＰＤ）、４－フェニル－４’－（９－フェニルフルオレン－９－イル）トリフェニルアミン（略称：ＢＡＦＬＰ）、４，４’－ビス［Ｎ－（９，９－ジメチルフルオレン－２－イル）－Ｎ－フェニルアミノ］ビフェニル（略称：ＤＦＬＤＰＢｉ）、４，４’，４’’－トリス（Ｎ，Ｎ－ジフェニルアミノ）トリフェニルアミン（略称：ＴＤＡＴＡ）、４，４’，４’’－トリス［Ｎ－（３－メチルフェニル）－Ｎ－フェニルアミノ］トリフェニルアミン（略称：ＭＴＤＡＴＡ）、４，４’－ビス［Ｎ－（スピロ－９，９’－ビフルオレン－２－イル）－Ｎ―フェニルアミノ］ビフェニル（略称：ＢＳＰＢ）などの芳香族アミン化合物等を用いることができる。ここに述べた物質は、主に１０－６ｃｍ２／（Ｖ・ｓ）以上の正孔移動度を有する物質である。 (hole transport layer)
The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) and N,N'-bis(3-methylphenyl)-N,N'- Diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4 , 4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino) ) triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis Aromatic amine compounds such as [N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. The substances described here mainly have a hole mobility of 10 −6 cm 2 /(V·s) or more.

　正孔輸送層には、ＣＢＰ、９－［４－（Ｎ－カルバゾリル）］フェニル－１０－フェニルアントラセン（ＣｚＰＡ）、９－フェニル－３－［４－（１０－フェニル－９－アントリル）フェニル］－９Ｈ－カルバゾール（ＰＣｚＰＡ）のようなカルバゾール誘導体や、ｔ－ＢｕＤＮＡ、ＤＮＡ、ＤＰＡｎｔｈのようなアントラセン誘導体を用いても良い。ポリ（Ｎ－ビニルカルバゾール）（略称：ＰＶＫ）やポリ（４－ビニルトリフェニルアミン）（略称：ＰＶＴＰＡ）等の高分子化合物を用いることもできる。 The hole transport layer contains CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl] Carbazole derivatives such as -9H-carbazole (PCzPA) and anthracene derivatives such as t-BuDNA, DNA, and DPAnth may also be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

　但し、電子よりも正孔の輸送性の高い物質であれば、これら以外のものを用いてもよい。なお、正孔輸送性の高い物質を含む層は、単層のものだけでなく、上記物質からなる層が二層以上積層したものとしてもよい。 However, materials other than these may be used as long as they have a higher transportability for holes than for electrons. Note that the layer containing a substance with high hole transport properties is not limited to a single layer, and may be a stack of two or more layers made of the above substance.

　正孔輸送層を二層以上配置する場合、エネルギーギャップのより大きい材料を発光層に近い側に配置することが好ましい。このような材料として、後記する実施例で用いた、ＨＴ－２が挙げられる。 When two or more hole transport layers are arranged, it is preferable to arrange a material with a larger energy gap on the side closer to the light emitting layer. An example of such a material is HT-2, which was used in Examples described later.

（電子輸送層）
　電子輸送層は、電子輸送性の高い物質を含む層である。電子輸送層には、１）アルミニウム錯体、ベリリウム錯体、亜鉛錯体等の金属錯体、２）イミダゾール誘導体、ベンゾイミダゾール誘導体、アジン誘導体、カルバゾール誘導体、フェナントロリン誘導体等の複素芳香族化合物、３）高分子化合物を使用することができる。具体的には低分子の有機化合物として、Ａｌｑ、トリス（４－メチル－８－キノリノラト）アルミニウム（略称：Ａｌｍｑ３）、ビス（１０－ヒドロキシベンゾ［ｈ］キノリナト）ベリリウム（略称：ＢｅＢｑ２）、ＢＡｌｑ、Ｚｎｑ、ＺｎＰＢＯ、ＺｎＢＴＺなどの金属錯体等を用いることができる。また、金属錯体以外にも、２－（４－ビフェニリル）－５－（４－ｔｅｒｔ－ブチルフェニル）－１，３，４－オキサジアゾール（略称：ＰＢＤ）、１，３－ビス［５－（ｐｔｅｒｔ－ブチルフェニル）－１，３，４－オキサジアゾール－２－イル］ベンゼン（略称：ＯＸＤ－７）、３－（４－ｔｅｒｔ－ブチルフェニル）－４－フェニル－５－（４－ビフェニリル）－１，２，４－トリアゾール（略称：ＴＡＺ）、３－（４－ｔｅｒｔ－ブチルフェニル）－４－（４－エチルフェニル）－５－（４－ビフェニリル）－１，２，４－トリアゾール（略称：ｐ－ＥｔＴＡＺ）、バソフェナントロリン（略称：ＢＰｈｅｎ）、バソキュプロイン（略称：ＢＣＰ）、４，４’－ビス（５－メチルベンゾオキサゾール－２－イル）スチルベン（略称：ＢｚＯｓ）などの複素芳香族化合物も用いることができる。本実施態様においては、ベンゾイミダゾール化合物を好適に用いることができる。ここに述べた物質は、主に１０－６ｃｍ２／（Ｖ・ｓ）以上の電子移動度を有する物質である。なお、正孔輸送性よりも電子輸送性の高い物質であれば、上記以外の物質を電子輸送層として用いてもよい。また、電子輸送層は、単層で構成されていてもよいし、上記物質からなる層が二層以上積層されて構成されていてもよい。 (electron transport layer)
The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer contains 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. can be used. Specifically, low-molecular organic compounds include Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq 3 ), bis(10-hydroxybenzo[h]quinolinato) beryllium (abbreviation: BeBq 2 ), Metal complexes such as BAlq, Znq, ZnPBO, ZnBTZ, etc. can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5- (ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4- biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4- Complex compounds such as triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) Aromatic compounds can also be used. In this embodiment, benzimidazole compounds can be suitably used. The substances described here mainly have an electron mobility of 10 −6 cm 2 /(V·s) or more. Note that any material other than the above may be used as the electron transport layer, as long as it has a higher electron transport property than hole transport property. Further, the electron transport layer may be composed of a single layer, or may be composed of two or more laminated layers made of the above substances.

　また、電子輸送層には、高分子化合物を用いることもできる。例えば、ポリ［（９，９－ジヘキシルフルオレン－２，７－ジイル）－ｃｏ－（ピリジン－３，５－ジイル）］（略称：ＰＦ－Ｐｙ）、ポリ［（９，９－ジオクチルフルオレン－２，７－ジイル）－ｃｏ－（２，２’－ビピリジン－６，６’－ジイル）］（略称：ＰＦ－ＢＰｙ）などを用いることができる。 Furthermore, a polymer compound can also be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2, ,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), etc. can be used.

（電子注入層）
　電子注入層は、電子注入性の高い物質を含む層である。電子注入層には、リチウム（Ｌｉ）、セシウム（Ｃｓ）、カルシウム（Ｃａ）、フッ化リチウム（ＬｉＦ）、フッ化セシウム（ＣｓＦ）、フッ化カルシウム（ＣａＦ２）、リチウム酸化物（ＬｉＯｘ）等のようなアルカリ金属、アルカリ土類金属、またはそれらの化合物を用いることができる。その他、電子輸送性を有する物質にアルカリ金属、アルカリ土類金属、またはそれらの化合物を含有させたもの、具体的にはＡｌｑ中にマグネシウム（Ｍｇ）を含有させたもの等を用いてもよい。なお、この場合には、陰極からの電子注入をより効率良く行うことができる。 (electron injection layer)
The electron injection layer is a layer containing a substance with high electron injection properties. The electron injection layer contains lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiOx), etc. Alkali metals, alkaline earth metals, or compounds thereof can be used. In addition, a material containing an alkali metal, an alkaline earth metal, or a compound thereof in a substance having electron transport properties, specifically, a material containing magnesium (Mg) in Alq, etc. may be used. Note that in this case, electron injection from the cathode can be performed more efficiently.

　あるいは、電子注入層に、有機化合物と電子供与体（ドナー）とを混合してなる複合材料を用いてもよい。このような複合材料は、電子供与体によって有機化合物に電子が発生するため、電子注入性および電子輸送性に優れている。この場合、有機化合物としては、発生した電子の輸送に優れた材料であることが好ましく、具体的には、例えば上述した電子輸送層を構成する物質（金属錯体や複素芳香族化合物等）を用いることができる。電子供与体としては、有機化合物に対し電子供与性を示す物質であればよい。具体的には、アルカリ金属やアルカリ土類金属や希土類金属が好ましく、リチウム、セシウム、マグネシウム、カルシウム、エルビウム、イッテルビウム等が挙げられる。また、アルカリ金属酸化物やアルカリ土類金属酸化物が好ましく、リチウム酸化物、カルシウム酸化物、バリウム酸化物等が挙げられる。また、酸化マグネシウムのようなルイス塩基を用いることもできる。また、テトラチアフルバレン（略称：ＴＴＦ）等の有機化合物を用いることもできる。
（層形成方法）
　本実施形態の有機ＥＬ素子の各層の形成方法としては、上記で特に言及した以外には制限されないが、真空蒸着法、スパッタリング法、プラズマ法、イオンプレーティング法などの乾式成膜法や、スピンコーティング法、ディッピング法、フローコーティング法、インクジェット法などの湿式成膜法などの公知の方法を採用することができる。 Alternatively, a composite material made of a mixture of an organic compound and an electron donor may be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting generated electrons, and specifically, for example, the above-mentioned substances (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer are used. be able to. The electron donor may be any substance that exhibits electron-donating properties to organic compounds. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Moreover, alkali metal oxides and alkaline earth metal oxides are preferable, and examples thereof include lithium oxide, calcium oxide, barium oxide, and the like. Additionally, Lewis bases such as magnesium oxide can also be used. Moreover, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.
(Layer formation method)
Methods for forming each layer of the organic EL element of this embodiment are not limited to those specifically mentioned above, but dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating, and spin Known methods such as coating methods, dipping methods, flow coating methods, wet film forming methods such as inkjet methods can be employed.

（膜厚）
　本実施形態の有機ＥＬ素子の各有機層の膜厚は、上記で特に言及した以外には制限されないが、一般に膜厚が薄すぎるとピンホール等の欠陥が生じやすく、逆に厚すぎると高い印加電圧が必要となり効率が悪くなるため、通常は数ｎｍから１μｍの範囲が好ましい。 (film thickness)
The film thickness of each organic layer of the organic EL element of this embodiment is not limited except as specifically mentioned above, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur; Since an applied voltage is required and efficiency deteriorates, the range of from several nm to 1 μm is usually preferable.

〔第二実施形態〕
　第二実施形態の有機ＥＬ素子の構成について説明する。第二実施形態の説明において第一実施形態と同一の構成要素は、同一符号や名称を付す等して説明を省略もしくは簡略化する。また、第二実施形態では、特に言及されない材料や化合物については、第一実施形態で説明した材料や化合物と同様の材料や化合物を用いることができる。 [Second embodiment]
The structure of the organic EL element of the second embodiment will be explained. In the description of the second embodiment, the same components as those in the first embodiment will be given the same reference numerals and names, and the description will be omitted or simplified. Furthermore, in the second embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first embodiment can be used.

　第二実施形態の有機ＥＬ素子は、発光層が、さらに蛍光発光性の化合物Ｍ１を含んでいる点で、第一実施形態の有機ＥＬ素子と異なる。その他の点については第一実施形態と同様である。
　第二実施形態の一態様において、発光層は、前記一般式（１－１）または（１－２）で表される化合物Ｍ３と、遅延蛍光性の化合物Ｍ２と、蛍光発光性の化合物Ｍ１とを含む。
　第二実施形態の一態様において、化合物Ｍ１は、ドーパント材料であることが好ましく、化合物Ｍ２は、ホスト材料であることが好ましく、化合物Ｍ３はホスト材料であることが好ましい。化合物Ｍ２及び化合物Ｍ３の一方を第一のホスト材料と称し、他方を第二のホスト材料と称する場合もある。 The organic EL device of the second embodiment differs from the organic EL device of the first embodiment in that the light emitting layer further contains a fluorescent compound M1. Other points are similar to the first embodiment.
In one aspect of the second embodiment, the light-emitting layer includes a compound M3 represented by the general formula (1-1) or (1-2), a delayed fluorescent compound M2, and a fluorescent compound M1. including.
In one aspect of the second embodiment, compound M1 is preferably a dopant material, compound M2 is preferably a host material, and compound M3 is preferably a host material. One of compound M2 and compound M3 may be referred to as a first host material, and the other may be referred to as a second host material.

（化合物Ｍ１）
　本実施形態の発光層は、蛍光発光性の化合物Ｍ１を含む。
　本実施形態の化合物Ｍ１は、燐光発光性の金属錯体ではない。本実施形態の化合物Ｍ１は、重金属錯体ではないことが好ましい。また、本実施形態の化合物Ｍ１は、金属錯体ではないことが好ましい。
　また、本実施形態の化合物Ｍ１は、熱活性化遅延蛍光性を示さない化合物であることが好ましい。 (Compound M1)
The light-emitting layer of this embodiment contains a fluorescent compound M1.
Compound M1 of this embodiment is not a phosphorescent metal complex. It is preferable that the compound M1 of this embodiment is not a heavy metal complex. Moreover, it is preferable that the compound M1 of this embodiment is not a metal complex.
Moreover, it is preferable that the compound M1 of this embodiment is a compound that does not exhibit heat-activated delayed fluorescence.

　本実施形態の化合物Ｍ１としては、蛍光発光性材料を用いることができる。蛍光発光性材料としては、具体的には、例えば、ビスアリールアミノナフタレン誘導体、アリール置換ナフタレン誘導体、ビスアリールアミノアントラセン誘導体、アリール置換アントラセン誘導体、ビスアリールアミノピレン誘導体、アリール置換ピレン誘導体、ビスアリールアミノクリセン誘導体、アリール置換クリセン誘導体、ビスアリールアミノフルオランテン誘導体、アリール置換フルオランテン誘導体、インデノペリレン誘導体、アセナフトフルオランテン誘導体、ホウ素原子を含む化合物、ピロメテンホウ素錯体化合物、ピロメテン骨格を有する化合物、ピロメテン骨格を有する化合物の金属錯体、ジケトピロロピロール誘導体、ペリレン誘導体、およびナフタセン誘導体などが挙げられる。 A fluorescent material can be used as the compound M1 of this embodiment. Specific examples of the fluorescent material include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, and bisarylaminopyrene derivatives. Chrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing a boron atom, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, Examples include metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

　化合物Ｍ１が蛍光発光性の化合物である場合、化合物Ｍ１は、最大ピーク波長が、４００ｎｍ以上７００ｎｍ以下の発光を示すことが好ましい。
　本明細書において、最大ピーク波長とは、測定対象化合物が１０－６モル／リットル以上１０－５モル／リットル以下の濃度で溶解しているトルエン溶液について、測定した蛍光スペクトルにおける発光強度が最大となる蛍光スペクトルのピーク波長をいう。測定装置は、分光蛍光光度計（日立ハイテクサイエンス社製、Ｆ－７０００）を用いる。 When compound M1 is a fluorescent compound, compound M1 preferably emits light with a maximum peak wavelength of 400 nm or more and 700 nm or less.
In this specification, the maximum peak wavelength refers to the maximum emission intensity in the measured fluorescence spectrum of a toluene solution in which the target compound is dissolved at a concentration of 10 -6 mol/liter or more and 10 -5 mol/liter or less. The peak wavelength of the fluorescence spectrum. A spectrofluorophotometer (manufactured by Hitachi High-Tech Science Co., Ltd., F-7000) is used as the measuring device.

　化合物Ｍ１は、赤色の発光又は緑色の発光を示すことが好ましい。
　本明細書において、赤色の発光とは、蛍光スペクトルの最大ピーク波長が６００ｎｍ以上６６０ｎｍ以下の範囲内である発光をいう。
　化合物Ｍ１が赤色の蛍光発光性の化合物である場合、化合物Ｍ１の最大ピーク波長は、好ましくは６００ｎｍ以上６６０ｎｍ以下、より好ましくは６００ｎｍ以上６４０ｎｍ以下、さらに好ましくは６１０ｎｍ以上６３０ｎｍ以下である。
　本明細書において、緑色の発光とは、蛍光スペクトルの最大ピーク波長が５００ｎｍ以上５６０ｎｍ以下の範囲内である発光をいう。
　化合物Ｍ１が緑色の蛍光発光性の化合物である場合、化合物Ｍ１の最大ピーク波長は、好ましくは５００ｎｍ以上５６０ｎｍ以下、より好ましくは５００ｎｍ以上５４０ｎｍ以下、さらに好ましくは５１０ｎｍ以上５４０ｎｍ以下である。
　本明細書において、青色の発光とは、蛍光スペクトルの最大ピーク波長が４３０ｎｍ以上４８０ｎｍ以下の範囲内である発光をいう。
　化合物Ｍ１が青色の蛍光発光性の化合物である場合、化合物Ｍ１の最大ピーク波長は、好ましくは４３０ｎｍ以上４８０ｎｍ以下、より好ましくは４４０ｎｍ以上４８０ｎｍ以下である。 Compound M1 preferably emits red or green light.
In this specification, red light emission refers to light emission in which the maximum peak wavelength of the fluorescence spectrum is within the range of 600 nm or more and 660 nm or less.
When compound M1 is a red fluorescent compound, the maximum peak wavelength of compound M1 is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and even more preferably 610 nm or more and 630 nm or less.
In this specification, green light emission refers to light emission in which the maximum peak wavelength of the fluorescence spectrum is within the range of 500 nm or more and 560 nm or less.
When compound M1 is a green fluorescent compound, the maximum peak wavelength of compound M1 is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and still more preferably 510 nm or more and 540 nm or less.
In this specification, blue light emission refers to light emission in which the maximum peak wavelength of the fluorescence spectrum is within the range of 430 nm or more and 480 nm or less.
When compound M1 is a blue fluorescent compound, the maximum peak wavelength of compound M1 is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.

　有機ＥＬ素子から発光する光の最大ピーク波長の測定は、以下のようにして行う。
　電流密度が１０ｍＡ／ｃｍ２となるように有機ＥＬ素子に電圧を印加した時の分光放射輝度スペクトルを分光放射輝度計ＣＳ－２０００（コニカミノルタ社製）で計測する。
　得られた分光放射輝度スペクトルにおいて、発光強度が最大となる発光スペクトルのピーク波長を測定し、これを最大ピーク波長（単位：ｎｍ）とする。 The maximum peak wavelength of light emitted from an organic EL element is measured as follows.
A spectral radiance spectrum is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta) when a voltage is applied to the organic EL element so that the current density is 10 mA/cm 2 .
In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity becomes maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).

（一般式（２Ａ）で表される化合物）
　本実施形態において、化合物Ｍ１は、下記一般式（２Ａ）で表される化合物であることが好ましい。化合物Ｍ１は、最大ピーク波長が５００ｎｍ以上５６０ｎｍ以下の発光を示す化合物であることが好ましい。 (Compound represented by general formula (2A))
In this embodiment, compound M1 is preferably a compound represented by the following general formula (2A). Compound M1 is preferably a compound that emits light with a maximum peak wavelength of 500 nm or more and 560 nm or less.

（前記一般式（２Ａ）において、
　Ｚａ環、Ｚｂ環及びＺｃ環は、それぞれ独立に、
　　置換もしくは無置換の環形成炭素数６～５０の芳香族炭化水素環、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環であり、
　Ｒａは、前記Ｚａ環又は前記Ｚｂ環と結合して置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成せず、
　Ｒｂは、前記Ｚａ環又は前記Ｚｃ環と結合して置換もしくは無置換の複素環を形成するか、あるいは置換もしくは無置換の複素環を形成せず、
　前記置換もしくは無置換の複素環を形成しないＲａ及びＲｂは、それぞれ独立に、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の炭素数２～５０のアルケニル基、
　　置換もしくは無置換の炭素数２～５０のアルキニル基、
　　置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環基である。） (In the general formula (2A),
The Za ring, Zb ring, and Zc ring are each independently,
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms,
Ra combines with the Za ring or the Zb ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle,
Rb combines with the Za ring or the Zc ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle,
The above-mentioned Ra and Rb which do not form a substituted or unsubstituted heterocycle are each independently,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. )

（一般式（Ｄ１１）で表される化合物）
　本実施形態において、化合物Ｍ１は、下記一般式（Ｄ１１）で表される化合物であることも好ましい。前記一般式（２Ａ）で表される化合物は、下記一般式（Ｄ１１）で表される化合物であることも好ましい。 (Compound represented by general formula (D11))
In this embodiment, it is also preferable that the compound M1 is a compound represented by the following general formula (D11). The compound represented by the general formula (2A) is also preferably a compound represented by the following general formula (D11).

（前記一般式（Ｄ１１）において、Ｒｂは、前記一般式（２Ａ）におけるＲｂと同義であり、
　Ｘ１は、ＣＲ１または窒素原子であり、
　Ｘ２は、ＣＲ２または窒素原子であり、
　Ｘ３は、ＣＲ３または窒素原子であり、
　Ｘ４は、ＣＲ４または窒素原子であり、
　Ｘ５は、ＣＲ５または窒素原子であり、
　Ｘ６は、ＣＲ６または窒素原子であり、
　Ｘ７は、ＣＲ７であるか、窒素原子であるか、またはＸ８と単結合で結合する炭素原子であり、
　Ｘ８は、ＣＲ８であるか、窒素原子であるか、またはＸ７と単結合で結合する炭素原子であり、
　Ｘ９は、ＣＲ９または窒素原子であり、
　Ｘ１０は、ＣＲ１０または窒素原子であり、
　Ｘ１１は、ＣＲ１１または窒素原子であり、
　Ｘ１２は、ＣＲ１２または窒素原子であり、
　Ｑは、ＣＲＱまたは窒素原子であり、
　Ｒ１～Ｒ６並びにＲ９～Ｒ１１のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　Ｒ３、Ｒ４およびＲｂのうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　　Ｒ３、Ｒ４およびＲｂのうちの隣接する２つ以上からなる組の１組以上が互いに結合して形成された単環又は縮合環における少なくとも一つの水素は、
　　炭素数１～５０のアルキル基、
　　環形成炭素数６～５０のアリール基、
　　環形成原子数５～５０の複素環基、
　　－Ｏ－（Ｒ９２０）で表される基、および
　　－Ｎ（Ｒ９２１）（Ｒ９２２）で表される基からなる群から選択される少なくともいずれかの置換基で置換されていているか、もしくは置換されておらず、
当該置換基における少なくとも一つの水素は、環形成炭素数６～５０のアリール基または炭素数１～５０のアルキル基で置換されているか、もしくは置換されておらず、
　前記置換もしくは無置換の単環を形成せず、かつ、前記置換もしくは無置換の縮合環を形成しないＲ１～Ｒ１１、並びにＲ１２～Ｒ１３、およびＲＱは、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の炭素数２～５０のアルケニル基、
　　置換もしくは無置換の炭素数２～５０のアルキニル基、
　　置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
　　－Ｓｉ（Ｒ９１１）（Ｒ９１２）（Ｒ９１３）で表される基、
　　－Ｏ－（Ｒ９１４）で表される基、
　　－Ｓ－（Ｒ９１５）で表される基、
　　－Ｎ（Ｒ９１６）（Ｒ９１７）で表される基、
　　置換もしくは無置換の炭素数７～５０のアラルキル基、
　　－Ｃ（＝Ｏ）Ｒ９１８で表される基、
　　－ＣＯＯＲ９１９で表される基、
　　ハロゲン原子、
　　シアノ基、
　　ニトロ基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環基であり、
　前記置換もしくは無置換の単環を形成せず、かつ、前記置換もしくは無置換の縮合環を形成しないＲｂは、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の炭素数２～５０のアルケニル基、
　　置換もしくは無置換の炭素数２～５０のアルキニル基、
　　置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、または
　　置換もしくは無置換の環形成原子数５～５０の複素環基であり、
　Ｒ９１１～Ｒ９２２は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環基であり、
　Ｒ９１１が複数存在する場合、複数のＲ９１１は、互いに同一であるか又は異なり、
　Ｒ９１２が複数存在する場合、複数のＲ９１２は、互いに同一であるか又は異なり、
　Ｒ９１３が複数存在する場合、複数のＲ９１３は、互いに同一であるか又は異なり、
　Ｒ９１４が複数存在する場合、複数のＲ９１４は、互いに同一であるか又は異なり、
　Ｒ９１５が複数存在する場合、複数のＲ９１５は、互いに同一であるか又は異なり、
　Ｒ９１６が複数存在する場合、複数のＲ９１６は、互いに同一であるか又は異なり、
　Ｒ９１７が複数存在する場合、複数のＲ９１７は、互いに同一であるか又は異なり、
　Ｒ９１８が複数存在する場合、複数のＲ９１８は、互いに同一であるか又は異なり、
　Ｒ９１９が複数存在する場合、複数のＲ９１９は、互いに同一であるか又は異なり、
　Ｒ９２０が複数存在する場合、複数のＲ９２０は、互いに同一であるか又は異なり、
　Ｒ９２１が複数存在する場合、複数のＲ９２１は、互いに同一であるか又は異なり、
　Ｒ９２２が複数存在する場合、複数のＲ９２２は、互いに同一であるか又は異なる。） (In the general formula (D11), Rb has the same meaning as Rb in the general formula (2A),
X 1 is CR 1 or a nitrogen atom,
X 2 is CR 2 or a nitrogen atom,
X 3 is CR 3 or a nitrogen atom,
X 4 is CR 4 or a nitrogen atom,
X 5 is CR 5 or a nitrogen atom,
X 6 is CR 6 or a nitrogen atom,
X 7 is CR 7 , a nitrogen atom, or a carbon atom bonded to X 8 with a single bond,
X 8 is CR 8 , a nitrogen atom, or a carbon atom bonded to X 7 with a single bond,
X 9 is CR 9 or a nitrogen atom,
X 10 is CR 10 or a nitrogen atom,
X 11 is CR 11 or a nitrogen atom,
X 12 is CR 12 or a nitrogen atom,
Q is CR Q or a nitrogen atom,
One or more sets of adjacent two or more of R 1 to R 6 and R 9 to R 11 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
One or more sets of two or more adjacent ones of R 3 , R 4 and Rb are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
At least one hydrogen in a monocyclic or condensed ring formed by bonding one or more of a group consisting of two or more adjacent ones of R 3 , R 4 and Rb to each other is
an alkyl group having 1 to 50 carbon atoms,
an aryl group having 6 to 50 ring carbon atoms;
a heterocyclic group having 5 to 50 ring atoms;
is substituted with at least one substituent selected from the group consisting of a group represented by -O-(R 920 ) and a group represented by -N(R 921 )(R 922 ), or not replaced,
At least one hydrogen in the substituent is substituted with an aryl group having 6 to 50 ring carbon atoms or an alkyl group having 1 to 50 carbon atoms, or is not substituted,
R 1 to R 11 , R 12 to R 13 , and R Q that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted fused ring are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A group represented by -Si(R 911 )(R 912 )(R 913 ),
A group represented by -O-(R 914 ),
A group represented by -S-(R 915 ),
A group represented by -N(R 916 )(R 917 ),
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
-C(=O)R A group represented by 918 ,
- A group represented by COOR 919 ,
halogen atom,
cyano group,
nitro group,
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
Rb that does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
R 911 to R 922 are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
When a plurality of R 911s exist, the plurality of R 911s are the same or different from each other,
When a plurality of R 912s exist, the plurality of R 912s are the same or different from each other,
When a plurality of R 913s exist, the plurality of R 913s are the same or different from each other,
When a plurality of R 914s exist, the plurality of R 914s are the same or different from each other,
When a plurality of R 915s exist, the plurality of R 915s are the same or different from each other,
When a plurality of R 916s exist, the plurality of R 916s are the same or different from each other,
When a plurality of R 917s exist, the plurality of R 917s are the same or different from each other,
When a plurality of R 918s exist, the plurality of R 918s are the same or different from each other,
When a plurality of R 919s exist, the plurality of R 919s are the same or different from each other,
When a plurality of R 920s exist, the plurality of R 920s are the same or different from each other,
When a plurality of R 921s exist, the plurality of R 921s are the same or different from each other,
When a plurality of R 922s exist, the plurality of R 922s are the same or different from each other. )

　前記一般式（Ｄ１１）で表される化合物は、下記一般式（Ｄ１３）で表されることも好ましい。 The compound represented by the general formula (D11) is also preferably represented by the following general formula (D13).

（前記一般式（Ｄ１３）において、
　Ｒ１～Ｒ３、Ｒ５～Ｒ１３およびＲＱは、それぞれ独立に、前記一般式（Ｄ１１）におけるＲ１～Ｒ３、Ｒ５～Ｒ１３およびＲＱと同義であり、
　ＲＡ１～ＲＡ４のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　前記置換もしくは無置換の単環を形成せず、かつ、前記置換もしくは無置換の縮合環を形成しないＲＡ１～ＲＡ４は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の炭素数２～５０のアルケニル基、
　　置換もしくは無置換の炭素数２～５０のアルキニル基、
　　置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
　　置換もしくは無置換の炭素数７～５０のアラルキル基、
　　－Ｓｉ（Ｒ９３１）（Ｒ９３２）（Ｒ９３３）で表される基、
　　－Ｏ－（Ｒ９３４）で表される基、
　　－Ｓ－（Ｒ９３５）で表される基、
　　－Ｎ（Ｒ９３６）（Ｒ９３７）で表される基、
　　置換もしくは無置換の炭素数７～５０のアラルキル基、
　　－Ｃ（＝Ｏ）Ｒ９３８で表される基、
　　－ＣＯＯＲ９３９で表される基、
　　ハロゲン原子、
　　シアノ基、
　　ニトロ基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環基であり、
　Ｒ９３１～Ｒ９３９は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環基であり、
　Ｒ９３１が複数存在する場合、複数のＲ９３１は、互いに同一であるか又は異なり、
　Ｒ９３２が複数存在する場合、複数のＲ９３２は、互いに同一であるか又は異なり、
　Ｒ９３３が複数存在する場合、複数のＲ９３３は、互いに同一であるか又は異なり、
　Ｒ９３４が複数存在する場合、複数のＲ９３４は、互いに同一であるか又は異なり、
　Ｒ９３５が複数存在する場合、複数のＲ９３５は、互いに同一であるか又は異なり、
　Ｒ９３６が複数存在する場合、複数のＲ９３６は、互いに同一であるか又は異なり、
　Ｒ９３７が複数存在する場合、複数のＲ９３７は、互いに同一であるか又は異なり、
　Ｒ９３８が複数存在する場合、複数のＲ９３８は、互いに同一であるか又は異なり、
　Ｒ９３９が複数存在する場合、複数のＲ９３９は、互いに同一であるか又は異なる。） (In the general formula (D13),
R 1 to R 3 , R 5 to R 13 and R Q are each independently synonymous with R 1 to R 3 , R 5 to R 13 and R Q in the general formula (D11),
One or more sets of two or more adjacent ones of R A1 to R A4 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R A1 to R A4 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted fused ring are each independently:
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
A group represented by -Si(R 931 )(R 932 )(R 933 ),
A group represented by -O-(R 934 ),
A group represented by -S-(R 935 ),
A group represented by -N(R 936 )(R 937 ),
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
-C(=O)R A group represented by 938 ,
- A group represented by COOR 939 ,
halogen atom,
cyano group,
nitro group,
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
R 931 to R 939 are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
When a plurality of R 931s exist, the plurality of R 931s are the same or different from each other,
When a plurality of R 932s exist, the plurality of R 932s are the same or different from each other,
When multiple R 933s exist, the multiple R 933s are the same or different,
When a plurality of R 934s exist, the plurality of R 934s are the same or different from each other,
When a plurality of R 935s exist, the plurality of R 935s are the same or different from each other,
When a plurality of R 936s exist, the plurality of R 936s are the same or different from each other,
When multiple R 937s exist, the multiple R 937s are the same or different,
When a plurality of R 938s exist, the plurality of R 938s are the same or different from each other,
When a plurality of R 939s exist, the plurality of R 939s are the same or different from each other. )

　前記一般式（Ｄ１１）で表される化合物は、下記一般式（Ｄ１３Ａ）で表されることも好ましい。 The compound represented by the general formula (D11) is also preferably represented by the following general formula (D13A).

（前記一般式（Ｄ１３Ａ）において、Ｒ１、Ｒ３、Ｒ５～Ｒ１３、ＲＱ及びＲＡ１～ＲＡ４は、それぞれ独立に、前記一般式（Ｄ１３）におけるＲ１、Ｒ３、Ｒ５～Ｒ１３、ＲＱ及びＲＡ１～ＲＡ４と同義であり、
　ＲＡ５～ＲＡ９のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲＡ５～ＲＡ９は、それぞれ独立に、前記一般式（Ｄ１３）中、前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲＡ１～ＲＡ４と同義である。） (In the general formula (D13A), R 1 , R 3 , R 5 to R 13 , R Q and R A1 to R A4 each independently represent R 1 , R 3 , R 5 in the general formula (D13) ~R 13 , R Q and R A1 ~ R A4 are synonymous,
One or more sets of two or more adjacent ones of R A5 to R A9 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R A5 to R A9 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring each independently represent the substituted or unsubstituted ring in the general formula (D13). It has the same meaning as R A1 to R A4 that do not form a single ring and do not form a substituted or unsubstituted fused ring. )

　なお、前記一般式（Ｄ１３）及び（Ｄ１３Ａ）において、例えば、Ｒ５及びＲ６からなる組が、互いに結合して、置換もしくは無置換の単環を形成するか、互いに結合して、置換もしくは無置換の縮合環を形成するか、又は互いに結合しない。 In general formulas (D13) and (D13A), for example, the set consisting of R 5 and R 6 may be bonded to each other to form a substituted or unsubstituted monocycle, or may be bonded to each other to form a substituted or unsubstituted monocycle. They form unsubstituted fused rings or do not bond to each other.

　前記一般式（Ｄ１１）で表される化合物において、Ｒ１～Ｒ１３及びＲＱは、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、または
　　置換もしくは無置換の環形成原子数５～５０のヘテロアリール基であることも好ましい。 In the compound represented by the general formula (D11), R 1 to R 13 and R Q are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
It is also preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

　前記一般式（Ｄ１１）で表される化合物において、Ｒ１～Ｒ１３及びＲＱは、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～２５のアルキル基、
　　置換もしくは無置換の環形成炭素数６～２５のアリール基、または
　　置換もしくは無置換の環形成原子数５～２５のヘテロアリール基であることも好ましい。 In the compound represented by the general formula (D11), R 1 to R 13 and R Q are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 25 carbon atoms,
It is also preferably a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

　前記一般式（Ｄ１３）及び（Ｄ１３Ａ）で表される化合物において、Ｒ１～Ｒ３、Ｒ５～Ｒ１３、ＲＱ及びＲＡ１～ＲＡ９は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、または
　　置換もしくは無置換の環形成原子数５～５０のヘテロアリール基であることも好ましい。 In the compounds represented by the general formulas (D13) and (D13A), R 1 to R 3 , R 5 to R 13 , R Q and R A1 to R A9 are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
It is also preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

　前記一般式（Ｄ１３）及び（Ｄ１３Ａ）で表される化合物において、Ｒ１～Ｒ３、Ｒ５～Ｒ１３、ＲＱ及びＲＡ１～ＲＡ９は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～２５のアルキル基、
　　置換もしくは無置換の環形成炭素数６～２５のアリール基、または
　　置換もしくは無置換の環形成原子数５～２５のヘテロアリール基であることも好ましい。 In the compounds represented by the general formulas (D13) and (D13A), R 1 to R 3 , R 5 to R 13 , R Q and R A1 to R A9 are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 25 carbon atoms,
It is also preferably a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

　前記一般式（Ｄ１１）で表される化合物は、下記一般式（Ｄ１４）で表されることも好ましい。 The compound represented by the general formula (D11) is also preferably represented by the following general formula (D14).

（前記一般式（Ｄ１４）で表される化合物において、Ｒ２、Ｒ６、Ｒ１３、ＲＱおよびＲＡ２は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～１０のアルキル基、
　　置換もしくは無置換の環形成炭素数６～１２のアリール基、または
　　置換もしくは無置換の環形成原子数５～１８のヘテロアリール基である。） (In the compound represented by the general formula (D14), R 2 , R 6 , R 13 , R Q and R A2 are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
A substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms. )

　前記一般式（Ｄ１４）において、Ｒ１３およびＲＱは、それぞれ独立に、
　　置換もしくは無置換の炭素数１～１０のアルキル基、
　　置換もしくは無置換のフェニル基、
　　置換もしくは無置換のナフチル基、または
　　置換もしくは無置換のジベンゾフラニル基であることが好ましい。 In the general formula (D14), R 13 and R Q are each independently,
Substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
substituted or unsubstituted phenyl group,
It is preferably a substituted or unsubstituted naphthyl group or a substituted or unsubstituted dibenzofuranyl group.

　前記一般式（Ｄ１４）で表される化合物において、Ｒ６およびＲＡ２は、それぞれ独立に、水素原子、または置換もしくは無置換の炭素数１～１０のアルキル基であることが好ましい。 In the compound represented by the general formula (D14), R 6 and R A2 are each independently preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

（一般式（１６）で表される化合物）
　本実施形態において、化合物Ｍ１は、下記一般式（１６）で表される化合物であることも好ましい。前記一般式（２Ａ）で表される化合物は、下記一般式（１６）で表される化合物であることも好ましい。 (Compound represented by general formula (16))
In this embodiment, it is also preferable that the compound M1 is a compound represented by the following general formula (16). The compound represented by the general formula (2A) is also preferably a compound represented by the following general formula (16).

（前記一般式（１６）で表される化合物において、
　Ｒ１６１～Ｒ１７７のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ１６１～Ｒ１７７は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の炭素数２～５０のアルケニル基、
　　置換もしくは無置換の炭素数２～５０のアルキニル基、
　　置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
　　置換もしくは無置換の炭素数７～５０のアラルキル基、
　　－Ｓｉ（Ｒ９６１）（Ｒ９６２）（Ｒ９６３）で表される基、
　　－Ｏ－（Ｒ９６４）で表される基、
　　－Ｓ－（Ｒ９６５）で表される基、
　　－Ｎ（Ｒ９６６）（Ｒ９６７）で表される基、
　　－Ｃ（＝Ｏ）Ｒ９６８で表される基、
　　－ＣＯＯＲ９６９で表される基、
　　ハロゲン原子、
　　シアノ基、
　　ニトロ基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環基であり、
　Ｒ９６１～Ｒ９６９は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環基であり、
　Ｒ９６１が複数存在する場合、複数のＲ９６１は、互いに同一であるか又は異なり、
　Ｒ９６２が複数存在する場合、複数のＲ９６２は、互いに同一であるか又は異なり、
　Ｒ９６３が複数存在する場合、複数のＲ９６３は、互いに同一であるか又は異なり、
　Ｒ９６４が複数存在する場合、複数のＲ９６４は、互いに同一であるか又は異なり、
　Ｒ９６５が複数存在する場合、複数のＲ９６５は、互いに同一であるか又は異なり、
　Ｒ９６６が複数存在する場合、複数のＲ９６６は、互いに同一であるか又は異なり、
　Ｒ９６７が複数存在する場合、複数のＲ９６７は、互いに同一であるか又は異なり、
　Ｒ９６８が複数存在する場合、複数のＲ９６８は、互いに同一であるか又は異なり、
　Ｒ９６９が複数存在する場合、複数のＲ９６９は、互いに同一であるか又は異なる。） (In the compound represented by the general formula (16),
One or more sets of two or more adjacent ones of R 161 to R 177 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 161 to R 177 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted fused ring are each independently:
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
A group represented by -Si(R 961 )(R 962 )(R 963 ),
A group represented by -O-(R 964 ),
A group represented by -S-(R 965 ),
A group represented by -N(R 966 )(R 967 ),
-C(=O)R A group represented by 968 ,
- A group represented by COOR 969 ,
halogen atom,
cyano group,
nitro group,
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
R 961 to R 969 are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
When a plurality of R 961s exist, the plurality of R 961s are the same or different from each other,
When a plurality of R 962s exist, the plurality of R 962s are the same or different from each other,
When a plurality of R 963s exist, the plurality of R 963s are the same or different from each other,
When a plurality of R 964s exist, the plurality of R 964s are the same or different from each other,
When a plurality of R 965s exist, the plurality of R 965s are the same or different from each other,
When a plurality of R 966s exist, the plurality of R 966s are the same or different from each other,
When multiple R 967s exist, the multiple R 967s are the same or different from each other,
When a plurality of R 968s exist, the plurality of R 968s are the same or different from each other,
When a plurality of R 969s exist, the plurality of R 969s are the same or different from each other. )

　前記一般式（１６）で表される化合物において、Ｒ１６１～Ｒ１７７は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、又は
　　置換もしくは無置換の炭素数１～３０のアルキル基であることが好ましい。 In the compound represented by the general formula (16), R 161 to R 177 are each independently,
hydrogen atom,
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
It is preferably a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

　前記一般式（１６）で表される化合物において、Ｒ１６８～Ｒ１７０のうち少なくとも一つは、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環基であることが好ましい。 In the compound represented by the general formula (16), at least one of R 168 to R 170 is
It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

　前記一般式（１６）で表される化合物において、Ｒ１６１～Ｒ１７７は、それぞれ独立に、
　　水素原子、又は
　　置換もしくは無置換の環形成炭素数６～３０のアリール基であることが好ましい。 In the compound represented by the general formula (16), R 161 to R 177 are each independently,
It is preferably a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

　前記一般式（１６）で表される化合物において、Ｒ１６１～Ｒ１７７は、水素原子であることも好ましい。 In the compound represented by the general formula (16), R 161 to R 177 are also preferably hydrogen atoms.

　前記一般式（１６）で表される化合物において、Ｒ１６１～Ｒ１７７のうちの隣接する２つ以上からなる組の少なくとも１組が互いに結合して、下記一般式（１６Ａ）で表される環を形成することも好ましい。 In the compound represented by the general formula (16), at least one set of two or more adjacent ones of R 161 to R 177 is bonded to each other to form a ring represented by the general formula (16A) below. It is also preferable to form

（前記一般式（１６Ａ）における点線は、接合部位を意味し、
　ＲＸ１～ＲＸ４は、それぞれ独立に、
　　水素原子、
　　置換もしくは無置換の炭素数１～５０のアルキル基、
　　置換もしくは無置換の炭素数２～５０のアルケニル基、
　　置換もしくは無置換の炭素数２～５０のアルキニル基、
　　置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
　　置換もしくは無置換の炭素数７～５０のアラルキル基、
　　－Ｓｉ（Ｒ９６１）（Ｒ９６２）（Ｒ９６３）で表される基、
　　－Ｏ－（Ｒ９６４）で表される基、
　　－Ｓ－（Ｒ９６５）で表される基、
　　－Ｎ（Ｒ９６６）（Ｒ９６７）で表される基、
　　－Ｃ（＝Ｏ）Ｒ９６８で表される基、
　　－ＣＯＯＲ９６９で表される基、
　　ハロゲン原子、
　　シアノ基、
　　ニトロ基、
　　置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
　　置換もしくは無置換の環形成原子数５～５０の複素環基である。） (The dotted line in the general formula (16A) means the joining site,
R X1 to R X4 are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,
A group represented by -Si(R 961 )(R 962 )(R 963 ),
A group represented by -O-(R 964 ),
A group represented by -S-(R 965 ),
A group represented by -N(R 966 )(R 967 ),
-C(=O)R A group represented by 968 ,
- A group represented by COOR 969 ,
halogen atom,
cyano group,
nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. )

　ＲＸ１が複数存在する場合、複数のＲＸ１は、互いに同一であるか又は異なり、
　ＲＸ２が複数存在する場合、複数のＲＸ２は、互いに同一であるか又は異なり、
　ＲＸ３が複数存在する場合、複数のＲＸ３は、互いに同一であるか又は異なり、
　ＲＸ４が複数存在する場合、複数のＲＸ４は、互いに同一であるか又は異なる。 When there are multiple R X1s , the multiple R X1s are the same or different,
When a plurality of R X2s exist, the plurality of R X2s are the same or different from each other,
When a plurality of R X3s exist, the plurality of R X3s are the same or different from each other,
When a plurality of R X4s exist, the plurality of R X4s are the same or different from each other.

　前記一般式（１６）において、
　Ｒ１６１およびＲ１６２からなる組、
　Ｒ１６５およびＲ１６６からなる組、
　Ｒ１７２およびＲ１７３からなる組、並びに
　Ｒ１７６およびＲ１７７からなる組の少なくとも１つの組が互いに結合して、前記一般式（１６Ａ）で表される環を形成することも好ましい。 In the general formula (16),
A set consisting of R 161 and R 162 ,
A set consisting of R 165 and R 166 ,
It is also preferred that at least one of the group consisting of R 172 and R 173 and the group consisting of R 176 and R 177 combine with each other to form a ring represented by the general formula (16A).

　前記一般式（１６）において、Ｒ１６１およびＲ１６２からなる組、並びにＲ１７６およびＲ１７７からなる組が同時に前記一般式（１６Ａ）で表される環を形成しないことが好ましい。 In the general formula (16), it is preferable that the group consisting of R 161 and R 162 and the group consisting of R 176 and R 177 do not simultaneously form a ring represented by the general formula (16A).

　前記一般式（１６）において、Ｒ１６５およびＲ１６６からなる組が互いに結合して、前記一般式（１６Ａ）で表される環を形成すること、並びにＲ１７２およびＲ１７３からなる組が互いに結合して、前記一般式（１６Ａ）で表される環を形成することも好ましく、この場合、化合物Ｍ１は、下記一般式（１６１）で表される。 In the general formula (16), the group consisting of R 165 and R 166 bond to each other to form a ring represented by the general formula (16A), and the group consisting of R 172 and R 173 bond to each other. It is also preferable to form a ring represented by the general formula (16A) above, and in this case, compound M1 is represented by the following general formula (161).

　前記一般式（１６）で表される化合物は、下記一般式（１６１）で表される化合物であることも好ましい。 The compound represented by the general formula (16) is also preferably a compound represented by the following general formula (161).

（前記一般式（１６１）において、Ｒ１６１～Ｒ１６４、Ｒ１６７～Ｒ１７１、Ｒ１７４～Ｒ１７７及びＲＸ１～ＲＸ４は、それぞれ独立に、前記一般式（１６）におけるＲ１６１～Ｒ１６４、Ｒ１６７～Ｒ１７１、Ｒ１７４～Ｒ１７７及び前記一般式（１６Ａ）におけるＲＸ１～ＲＸ４と同義である。） (In the general formula (161), R 161 to R 164 , R 167 to R 171 , R 174 to R 177 and R X1 to R X4 each independently represent R 161 to R 164 in the general formula (16). , R 167 to R 171 , R 174 to R 177 and R X1 to R X4 in the general formula (16A) above.)

　前記一般式（１６）で表される化合物は、下記一般式（１６２）で表される化合物であることも好ましい。 The compound represented by the general formula (16) is also preferably a compound represented by the following general formula (162).

（前記一般式（１６２）において、Ｒ１６１～Ｒ１６３、Ｒ１６８～Ｒ１７０及びＲ１７５～Ｒ１７７は、それぞれ独立に、前記一般式（１６）におけるＲ１６１～Ｒ１６３、Ｒ１６８～Ｒ１７０及びＲ１７５～Ｒ１７７と同義である。） (In the general formula (162), R 161 to R 163 , R 168 to R 170 and R 175 to R 177 are each independently R 161 to R 163 , R 168 to R 170 in the general formula (16) and R 175 to R 177. )

　前記一般式（１６）で表される化合物は、下記一般式（１６３）で表される化合物であることも好ましい。 The compound represented by the general formula (16) is also preferably a compound represented by the following general formula (163).

（前記一般式（１６３）において、Ｒ１６２、Ｒ１６９及びＲ１７６は、それぞれ独立に、前記一般式（１６）におけるＲ１６２、Ｒ１６９及びＲ１７６と同義である。） (In the general formula (163), R 162 , R 169 and R 176 each independently have the same meaning as R 162 , R 169 and R 176 in the general formula (16).)

　化合物Ｍ１において、「置換もしくは無置換」と記載された基は、いずれも「無置換」の基であることも好ましい。 In compound M1, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

・化合物Ｍ１の製造方法
　化合物Ｍ１は、公知の方法により製造することができる。 -Method for producing compound M1 Compound M1 can be produced by a known method.

　本実施形態の化合物Ｍ１の具体例を以下に示す。ただし、本発明は、これら化合物の具体例に限定されない。
　なお、ピロメテン骨格中におけるホウ素原子と窒素原子との配位結合は、実線、破線、矢印、もしくは省略するなど、種々の表記方法がある。本明細書においては、実線で表すか、破線で表すか、又は記載を省略する。 Specific examples of compound M1 of this embodiment are shown below. However, the present invention is not limited to these specific examples of compounds.
Note that the coordinate bond between the boron atom and the nitrogen atom in the pyrromethene skeleton can be expressed in various ways, such as a solid line, a broken line, an arrow, or omitted. In this specification, it is represented by a solid line, a broken line, or the description is omitted.

Figure JPOXMLDOC01-appb-C000095
Figure JPOXMLDOC01-appb-C000095

Figure JPOXMLDOC01-appb-C000096
Figure JPOXMLDOC01-appb-C000096

Figure JPOXMLDOC01-appb-C000104
Figure JPOXMLDOC01-appb-C000104

Figure JPOXMLDOC01-appb-C000105
Figure JPOXMLDOC01-appb-C000105

Figure JPOXMLDOC01-appb-C000108
Figure JPOXMLDOC01-appb-C000108

＜発光層における化合物Ｍ３、化合物Ｍ２、及び化合物Ｍ１の関係＞
　本実施形態の有機ＥＬ素子において、化合物Ｍ１の一重項エネルギーＳ１（Ｍ１）と、前記化合物Ｍ２の一重項エネルギーＳ１（Ｍ２）とは、下記数式（数２）の関係を満たすことが好ましい。
　　　Ｓ１（Ｍ２）＞Ｓ１（Ｍ１）　　　（数２） <Relationship among compound M3, compound M2, and compound M1 in the light emitting layer>
In the organic EL device of this embodiment, it is preferable that the singlet energy S 1 (M1) of the compound M1 and the singlet energy S 1 (M2) of the compound M2 satisfy the following formula (Equation 2). .
S 1 (M2)>S 1 (M1) (Math. 2)

　また、化合物Ｍ３の一重項エネルギーＳ１（Ｍ３）は、化合物Ｍ１の一重項エネルギーＳ１（Ｍ１）よりも大きいことが好ましい。 Further, the singlet energy S 1 (M3) of the compound M3 is preferably larger than the singlet energy S 1 (M1) of the compound M1.

　化合物Ｍ３の一重項エネルギーＳ１（Ｍ３）と、化合物Ｍ２の一重項エネルギーＳ１（Ｍ２）と、化合物Ｍ１の一重項エネルギーＳ１（Ｍ１）とは、下記数式（数２Ａ）の関係を満たすことが好ましい。
　　　Ｓ１（Ｍ３）＞Ｓ１（Ｍ２）＞Ｓ１（Ｍ１）　　　…（数２Ａ） The singlet energy S 1 (M3) of compound M3, the singlet energy S 1 (M2) of compound M2, and the singlet energy S 1 (M1) of compound M1 satisfy the relationship of the following formula (Equation 2A). It is preferable.
S 1 (M3)>S 1 (M2)>S 1 (M1)...(Math 2A)

　本実施形態の有機ＥＬ素子を発光させたときに、発光層において、主に蛍光発光性の化合物Ｍ１が発光していることが好ましい。
　本実施形態の有機ＥＬ素子は、赤色発光または緑色発光することが好ましい。 When the organic EL element of this embodiment emits light, it is preferable that the fluorescent compound M1 mainly emits light in the light emitting layer.
The organic EL element of this embodiment preferably emits red light or green light.

・発光層における化合物の含有率
　発光層に含まれている化合物Ｍ３、化合物Ｍ２、及び化合物Ｍ１の含有率は、例えば、以下の範囲であることが好ましい。
　化合物Ｍ３の含有率は、１０質量％以上８０質量％以下であることが好ましい。
　化合物Ｍ２の含有率は、１０質量％以上８０質量％以下であることが好ましく、１０質量％以上６０質量％以下であることがより好ましく、２０質量％以上６０質量％以下であることがさらに好ましい。
　化合物Ｍ１の含有率は、０．０１質量％以上１０質量％以下であることが好ましく、０．０１質量％以上５質量％以下であることがより好ましく、０．０１質量％以上１質量％以下であることがさらに好ましい。
　発光層における化合物Ｍ３、化合物Ｍ２、及び化合物Ｍ１の合計含有率の上限は、１００質量％である。なお、本実施形態は、発光層に、化合物Ｍ３、化合物Ｍ２、及び化合物Ｍ１以外の材料が含まれることを除外しない。
　発光層は、化合物Ｍ３を１種のみ含んでもよいし、２種以上含んでもよい。発光層は、化合物Ｍ２を１種のみ含んでもよいし、２種以上含んでもよい。発光層は、化合物Ｍ１を１種のみ含んでもよいし、２種以上含んでもよい。 -Content of compounds in the light-emitting layer The content of the compound M3, compound M2, and compound M1 contained in the light-emitting layer is preferably within the following range, for example.
The content of compound M3 is preferably 10% by mass or more and 80% by mass or less.
The content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. .
The content of compound M1 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and 0.01% by mass or more and 1% by mass or less. It is more preferable that
The upper limit of the total content of compound M3, compound M2, and compound M1 in the light emitting layer is 100% by mass. Note that this embodiment does not exclude that the light-emitting layer includes materials other than compound M3, compound M2, and compound M1.
The light-emitting layer may contain only one type of compound M3, or may contain two or more types of compound M3. The light-emitting layer may contain only one type of compound M2, or may contain two or more types of compound M2. The light emitting layer may contain only one type of compound M1, or may contain two or more types of compound M1.

　図５は、発光層における化合物Ｍ３、化合物Ｍ２、及び化合物Ｍ１のエネルギー準位の関係の一例を示す図である。図５において、Ｓ０は、基底状態を表す。Ｓ１（Ｍ１）は、化合物Ｍ１の最低励起一重項状態を表し、Ｔ１（Ｍ１）は、化合物Ｍ１の最低励起三重項状態を表す。Ｓ１（Ｍ２）は、化合物Ｍ２の最低励起一重項状態を表し、Ｔ１（Ｍ２）は、化合物Ｍ２の最低励起三重項状態を表す。Ｓ１（Ｍ３）は、化合物Ｍ３の最低励起一重項状態を表し、Ｔ１（Ｍ３）は、化合物Ｍ３の最低励起三重項状態を表す。図５中のＳ１（Ｍ２）からＳ１（Ｍ１）へ向かう破線の矢印は、化合物Ｍ２の最低励起一重項状態から化合物Ｍ１の最低励起一重項状態へのフェルスター型エネルギー移動を表す。
　図５に示すように、化合物Ｍ２としてΔＳＴ（Ｍ２）の小さな化合物を用いると、最低励起三重項状態Ｔ１（Ｍ２）は、熱エネルギーにより、最低励起一重項状態Ｓ１（Ｍ２）に逆項間交差が可能である。そして、化合物Ｍ２の最低励起一重項状態Ｓ１（Ｍ２）から化合物Ｍ１へのフェルスター型エネルギー移動が生じ、最低励起一重項状態Ｓ１（Ｍ１）が生成する。この結果、化合物Ｍ１の最低励起一重項状態Ｓ１（Ｍ１）からの蛍光発光を観測することができる。このＴＡＤＦメカニズムによる遅延蛍光を利用することによっても、理論的に内部量子効率を１００％まで高めることができると考えられている。 FIG. 5 is a diagram showing an example of the relationship between the energy levels of compound M3, compound M2, and compound M1 in the light emitting layer. In FIG. 5, S0 represents the ground state. S1 (M1) represents the lowest excited singlet state of compound M1, and T1 (M1) represents the lowest excited triplet state of compound M1. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. The dashed arrow pointing from S1 (M2) to S1 (M1) in FIG. 5 represents Förster type energy transfer from the lowest excited singlet state of compound M2 to the lowest excited singlet state of compound M1.
As shown in Figure 5, when a compound with a small ΔST (M2) is used as the compound M2, the lowest excited triplet state T1 (M2) reversely intersystems crosses into the lowest excited singlet state S1 (M2) due to thermal energy. is possible. Then, a Förster type energy transfer occurs from the lowest excited singlet state S1 (M2) of the compound M2 to the compound M1, and the lowest excited singlet state S1 (M1) is generated. As a result, fluorescence emission from the lowest excited singlet state S1 (M1) of compound M1 can be observed. It is believed that the internal quantum efficiency can be theoretically increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

　第二実施形態の有機ＥＬ素子は、発光層に、遅延蛍光性の化合物Ｍ２と、前記化合物Ｍ２よりも大きな一重項エネルギーを有する化合物Ｍ３（前記一般式（１－１）または（１－２で表される化合物Ｍ３）と、遅延蛍光性の化合物Ｍ２よりも小さな一重項エネルギーを有する化合物Ｍ１とを含んでいる。
　第二実施形態によれば、高性能な有機ＥＬ素子が実現される。
　第二実施形態の一態様によれば、高効率で発光する有機ＥＬ素子が実現される。
　第二実施形態の一態様によれば、長寿命で発光する有機ＥＬ素子が実現される。
　第二実施形態の有機ＥＬ素子は、表示装置および発光装置等の電子機器に使用できる。 The organic EL device of the second embodiment includes a delayed fluorescent compound M2 and a compound M3 having a larger singlet energy than the compound M2 (in the general formula (1-1) or (1-2)) in the light emitting layer. Compound M3) and compound M1 having singlet energy smaller than delayed fluorescent compound M2.
According to the second embodiment, a high-performance organic EL element is realized.
According to one aspect of the second embodiment, an organic EL element that emits light with high efficiency is realized.
According to one aspect of the second embodiment, an organic EL element that emits light with a long life is realized.
The organic EL element of the second embodiment can be used in electronic devices such as display devices and light emitting devices.

〔第三実施形態〕
［電子機器］
　本実施形態に係る電子機器は、上述の実施形態のいずれかの有機ＥＬ素子を搭載している。電子機器としては、例えば、表示装置及び発光装置等が挙げられる。表示装置としては、例えば、表示部品（例えば、有機ＥＬパネルモジュール等）、テレビ、携帯電話、タブレット、及びパーソナルコンピュータ等が挙げられる。発光装置としては、例えば、照明及び車両用灯具等が挙げられる。 [Third embodiment]
[Electronics]
The electronic device according to this embodiment is equipped with the organic EL element according to any of the embodiments described above. Examples of electronic devices include display devices and light emitting devices. Examples of display devices include display components (eg, organic EL panel modules, etc.), televisions, mobile phones, tablets, personal computers, and the like. Examples of the light emitting device include lighting, vehicle lamps, and the like.

〔第四実施形態〕
［化合物］
　第四実施形態に係る化合物は、下記一般式（１００－１）～（１００－４）のいずれかで表される化合物である。
　第四実施形態に係る化合物のうち、下記一般式（１００－１）～（１００－３）で表される化合物は、第一実施形態で説明した一般式（１－１）で表される化合物の一態様であり、第一実施形態で説明した一般式（１００－１）～（１００－３）で表される化合物と同義である。
　第四実施形態に係る化合物のうち、下記一般式（１００－４）で表される化合物は、第一実施形態で説明した一般式（１－２）で表される化合物の一態様であり、第一実施形態で説明した一般式（１００－４Ａ）～（１００－４Ｄ）で表される化合物（ただし、Ｒ１００が、－Ｎ（Ｒｚ）２で表される基ではない）と同義である。 [Fourth embodiment]
[Compound]
The compound according to the fourth embodiment is a compound represented by any of the following general formulas (100-1) to (100-4).
Among the compounds according to the fourth embodiment, the compounds represented by the following general formulas (100-1) to (100-3) are the compounds represented by the general formula (1-1) explained in the first embodiment. This is one aspect of and has the same meaning as the compounds represented by general formulas (100-1) to (100-3) described in the first embodiment.
Among the compounds according to the fourth embodiment, the compound represented by the following general formula (100-4) is one embodiment of the compound represented by the general formula (1-2) explained in the first embodiment, It has the same meaning as the compound represented by the general formulas (100-4A) to (100-4D) described in the first embodiment (provided that R 100 is not a group represented by -N(Rz) 2 ) .

（前記一般式（１００－１）～（１００－３）において、Ａ、Ｌ１、Ｌ２、Ｙ１、Ｒ２１～Ｒ２８及びＲ１００は、それぞれ独立に、前記一般式（１－１）におけるＡ、Ｌ１、Ｌ２、Ｙ１、Ｒ２１～Ｒ２８及びＲ１００と同義である。）
（前記一般式（１００－４）において、Ａ、Ｌ１、Ｌ２、Ｙ１、Ｒ２１～Ｒ２８及びＲ１００は、それぞれ独立に、前記一般式（１－２）におけるＡ、Ｌ１、Ｌ２、Ｙ１、Ｒ２１～Ｒ２８及びＲ１００と同義であり、ただし、前記一般式（１００－４）中、Ｒ１００は、－Ｎ（Ｒｚ）２で表される基ではない。前記一般式（１００－４）中、＊は、Ｒ２１～Ｒ２４が結合する六員環の炭素原子のいずれか１つとの結合位置を表す。） (In the general formulas (100-1) to (100-3), A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 each independently represent the formula (1-1) It has the same meaning as A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 in.)
(In the general formula (100-4), A, L 1 , L 2 , Y 1 , R 21 to R 28 and R 100 each independently represent A, L 1 in the general formula (1-2), It has the same meaning as L 2 , Y 1 , R 21 to R 28 and R 100 , however, in the general formula (100-4), R 100 is not a group represented by -N(Rz) 2 . In general formula (100-4), * represents the bonding position with any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded.)

　前述の「一実施形態に係る化合物Ｍ３」におけるＬ１、Ｌ２、Ａ、Ｘ１、Ｙ１、Ｒ２１～Ｒ２８、Ｒ１１～Ｒ２０及びＲ１００等の要件は、以下の通り、第四実施形態に係る化合物にも適用できる。 The requirements for L 1 , L 2 , A, X 1 , Y 1 , R 21 to R 28 , R 11 to R 20 , R 100 , etc. in the aforementioned "Compound M3 according to one embodiment" are as follows. It is also applicable to the compounds according to the fourth embodiment.

　第四実施形態に係る化合物は、前記一般式（１００－１）、前記一般式（１００－２）、又は前記一般式（１００－３）で表される化合物であることが好ましい。 The compound according to the fourth embodiment is preferably a compound represented by the general formula (100-1), the general formula (100-2), or the general formula (100-3).

　第四実施形態に係る化合物の一態様において、Ｌ１及びＬ２は、それぞれ独立に、単結合、又は置換もしくは無置換のフェニレン基である。
　第四実施形態に係る化合物の一態様において、Ｌ１及びＬ２は、単結合である。
　第四実施形態に係る化合物の一態様において、Ａは、前記一般式（１１Ｆ）で表される基である。
　第四実施形態に係る化合物の一態様において、Ａは、前記一般式（１１Ｄ）で表される基である。
　第四実施形態に係る化合物の一態様において、Ｘ１は、硫黄原子である。
　第四実施形態に係る化合物の一態様において、Ｘ１は、酸素原子である。
　第四実施形態に係る化合物の一態様において、Ｙ１は、酸素原子である。
　第四実施形態に係る化合物の一態様において、Ｘ１は硫黄原子であり、Ｙ１は酸素原子である。第四実施形態に係る化合物の一態様において、Ｘ１及びＹ１は、酸素原子である。 In one aspect of the compound according to the fourth embodiment, L 1 and L 2 are each independently a single bond or a substituted or unsubstituted phenylene group.
In one aspect of the compound according to the fourth embodiment, L 1 and L 2 are single bonds.
In one aspect of the compound according to the fourth embodiment, A is a group represented by the general formula (11F).
In one aspect of the compound according to the fourth embodiment, A is a group represented by the general formula (11D).
In one aspect of the compound according to the fourth embodiment, X 1 is a sulfur atom.
In one aspect of the compound according to the fourth embodiment, X 1 is an oxygen atom.
In one aspect of the compound according to the fourth embodiment, Y 1 is an oxygen atom.
In one aspect of the compound according to the fourth embodiment, X 1 is a sulfur atom, and Y 1 is an oxygen atom. In one aspect of the compound according to the fourth embodiment, X 1 and Y 1 are oxygen atoms.

　第四実施形態に係る化合物の一態様において、Ｒ２１～Ｒ２８のうちの隣接する２つ以上からなる組が互いに結合しない。
　第四実施形態に係る化合物の一態様において、Ｒ２１～Ｒ２８は、それぞれ独立に、水素原子、又は置換もしくは無置換の環形成炭素数６～３０のアリール基（好ましくは置換もしくは無置換のフェニル基）である。
　第四実施形態に係る化合物の一態様において、Ｒ２１～Ｒ２８は、それぞれ独立に、水素原子、置換もしくは無置換のフェニル基、置換もしくは無置換のビフェニル基、置換もしくは無置換のカルバゾリル基、又は置換もしくは無置換のジベンゾフラニル基である。
　第四実施形態に係る化合物の一態様において、Ｒ２１～Ｒ２８は水素原子である。
　第四実施形態に係る化合物の一態様において、Ｒ２１～Ｒ２８の少なくとも１つは重水素原子である。 In one aspect of the compound according to the fourth embodiment, a group of two or more adjacent ones of R 21 to R 28 do not bond to each other.
In one aspect of the compound according to the fourth embodiment, R 21 to R 28 are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms). phenyl group).
In one aspect of the compound according to the fourth embodiment, R 21 to R 28 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group.
In one aspect of the compound according to the fourth embodiment, R 21 to R 28 are hydrogen atoms.
In one aspect of the compound according to the fourth embodiment, at least one of R 21 to R 28 is a deuterium atom.

　第四実施形態に係る化合物の一態様において、Ｒ１１～Ｒ２０のうちの隣接する２つ以上からなる組が互いに結合しない。
　第四実施形態に係る化合物の一態様において、Ｒ１１～Ｒ２０は、それぞれ独立に、水素原子、又は置換もしくは無置換の環形成炭素数６～３０のアリール基（好ましくは置換もしくは無置換のフェニル基）である。
　第四実施形態に係る化合物の一態様において、Ｒ１１～Ｒ２０は、それぞれ独立に、水素原子、置換もしくは無置換のフェニル基、置換もしくは無置換のビフェニル基、又は置換もしくは無置換のカルバゾリル基である。
　第四実施形態に係る化合物の一態様において、Ｒ１１～Ｒ２０は水素原子である。
　第四実施形態に係る化合物の一態様において、Ｒ１１～Ｒ２０の少なくとも１つは重水素原子である。 In one aspect of the compound according to the fourth embodiment, a set of two or more adjacent ones of R 11 to R 20 do not bond to each other.
In one aspect of the compound according to the fourth embodiment, R 11 to R 20 are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms). phenyl group).
In one aspect of the compound according to the fourth embodiment, R 11 to R 20 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted carbazolyl group. It is.
In one aspect of the compound according to the fourth embodiment, R 11 to R 20 are hydrogen atoms.
In one aspect of the compound according to the fourth embodiment, at least one of R 11 to R 20 is a deuterium atom.

　第四実施形態に係る化合物の一態様において、Ｒ１００は、それぞれ独立に、水素原子、又は置換もしくは無置換の環形成炭素数６～３０のアリール基（好ましくは置換もしくは無置換のフェニル基）である。
　第四実施形態に係る化合物の一態様において、Ｒ１００は、それぞれ独立に、水素原子、置換もしくは無置換のフェニル基、置換もしくは無置換のビフェニル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のカルバゾリル基、置換もしくは無置換の炭素数１～６のアルキル基、又はトリメチルシリル基である。
　第四実施形態に係る化合物の一態様において、Ｒ１００は水素原子である。
　第四実施形態に係る化合物の一態様において、複数のＲ１００のうち、少なくとも１つは重水素原子である。 In one aspect of the compound according to the fourth embodiment, R 100 is each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group) It is.
In one aspect of the compound according to the fourth embodiment, R 100 is each independently a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or an unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a trimethylsilyl group.
In one aspect of the compound according to the fourth embodiment, R 100 is a hydrogen atom.
In one aspect of the compound according to the fourth embodiment, at least one of the plurality of R 100 is a deuterium atom.

　第四実施形態によれば、高性能の有機ＥＬ素子を実現させることができる。
　第四実施形態の一態様によれば、高効率で発光する有機ＥＬ素子を実現させることができる。第四実施形態の一態様によれば、長寿命で発光する有機ＥＬ素子を実現させることができる。第四実施形態の化合物は、表示装置および発光装置等の電子機器に使用できる。 According to the fourth embodiment, a high-performance organic EL element can be realized.
According to one aspect of the fourth embodiment, an organic EL element that emits light with high efficiency can be realized. According to one aspect of the fourth embodiment, an organic EL element that emits light with a long life can be realized. The compound of the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

［有機ＥＬ素子］
　第四実施形態の一態様である有機ＥＬ素子は、第四実施形態の化合物（前記一般式（１００－１）～（１００－４）のいずれかで表される化合物）を、陽極および陰極の間に配置された有機層のうち、いずれかの層に含む有機ＥＬ素子である。
　第四実施形態の一態様である有機ＥＬ素子は、前記一般式（１００－１）、前記一般式（１００－２）、又は前記一般式（１００－３）で表される化合物を、陽極および陰極の間に配置された有機層のうち、いずれかの層に含む有機ＥＬ素子である。
　第四実施形態の化合物は、高性能の有機ＥＬ素子を実現させることのできる化合物である。したがって、第四実施形態の一態様である有機ＥＬ素子は、高性能である。第四実施形態の一態様である有機ＥＬ素子は、高効率で発光する。第四実施形態の一態様である有機ＥＬ素子は、長寿命で発光する。 [Organic EL element]
An organic EL device that is an aspect of the fourth embodiment uses the compound of the fourth embodiment (a compound represented by any one of the general formulas (100-1) to (100-4)) as an anode and a cathode. This is an organic EL element included in one of the organic layers arranged between them.
An organic EL device that is an aspect of the fourth embodiment includes a compound represented by the general formula (100-1), the general formula (100-2), or the general formula (100-3) at the anode and This is an organic EL element that is included in one of the organic layers arranged between cathodes.
The compound of the fourth embodiment is a compound that can realize a high-performance organic EL device. Therefore, the organic EL element that is one aspect of the fourth embodiment has high performance. The organic EL element that is one aspect of the fourth embodiment emits light with high efficiency. The organic EL element that is one aspect of the fourth embodiment emits light with a long lifetime.

　第四実施形態に係る化合物の具体例としては、例えば、第一実施形態において、化合物Ｍ３として例示した化合物と同様の化合物が挙げられる。ただし、本発明は、これら化合物の具体例に限定されない。 Specific examples of the compound according to the fourth embodiment include, for example, the same compound as the compound exemplified as compound M3 in the first embodiment. However, the present invention is not limited to these specific examples of compounds.

〔第五実施形態〕
〔有機ＥＬ素子用材料〕
　第五実施形態の有機ＥＬ素子用材料は、第四実施形態の化合物を含む。
　第五実施形態の有機ＥＬ素子用材料によれば、高性能の有機ＥＬ素子及び電子機器を実現させることができる。
　なお、第六実施形態の有機ＥＬ素子用材料は、さらにその他の化合物を含有していてもよい。第六実施形態の有機ＥＬ素子用材料が、さらにその他の化合物を含んでいる場合、該その他の化合物は、固体であっても液体であってもよい。 [Fifth embodiment]
[Materials for organic EL elements]
The organic EL element material of the fifth embodiment contains the compound of the fourth embodiment.
According to the organic EL element material of the fifth embodiment, a high-performance organic EL element and electronic device can be realized.
In addition, the organic EL element material of the sixth embodiment may further contain other compounds. When the organic EL element material of the sixth embodiment further contains other compounds, the other compounds may be solid or liquid.

〔実施形態の変形〕
　なお、本発明は、上述の実施形態に限定されず、本発明の目的を達成できる範囲での変更、改良等は、本発明に含まれる。 [Variation of embodiment]
It should be noted that the present invention is not limited to the above-described embodiments, and any changes, improvements, etc. that can achieve the purpose of the present invention are included in the present invention.

　例えば、発光層は、１層に限られず、複数の発光層が積層されていてもよい。有機ＥＬ素子が複数の発光層を有する場合、少なくとも１つの発光層が上記実施形態で説明した条件を満たしていればよい。例えば、その他の発光層が、蛍光発光型の発光層であっても、三重項励起状態から直接基底状態への電子遷移による発光を利用した燐光発光型の発光層であってもよい。
　また、有機ＥＬ素子が複数の発光層を有する場合、これらの発光層が互いに隣接して設けられていてもよいし、中間層を介して複数の発光ユニットが積層された、いわゆるタンデム型の有機ＥＬ素子であってもよい。 For example, the number of light emitting layers is not limited to one layer, and a plurality of light emitting layers may be stacked. When an organic EL element has a plurality of light emitting layers, it is sufficient that at least one light emitting layer satisfies the conditions described in the above embodiment. For example, the other light-emitting layer may be a fluorescent-type light-emitting layer or a phosphorescent-type light-emitting layer that utilizes light emission due to electronic transition directly from a triplet excited state to a ground state.
In addition, when the organic EL element has a plurality of light emitting layers, these light emitting layers may be provided adjacent to each other, or a so-called tandem type organic EL element may be provided in which a plurality of light emitting units are stacked with an intermediate layer interposed therebetween. It may also be an EL element.

　また、例えば、発光層の陽極側、及び陰極側の少なくとも一方に障壁層を隣接させて設けてもよい。障壁層は、発光層に接して配置され、正孔、電子、及び励起子の少なくともいずれかを阻止することが好ましい。
　例えば、発光層の陰極側で接して障壁層が配置された場合、当該障壁層は、電子を輸送し、かつ正孔が当該障壁層よりも陰極側の層（例えば、電子輸送層）に到達することを阻止する。有機ＥＬ素子が、電子輸送層を含む場合は、発光層と電子輸送層との間に当該障壁層を含むことが好ましい。
　また、発光層の陽極側で接して障壁層が配置された場合、当該障壁層は、正孔を輸送し、かつ電子が当該障壁層よりも陽極側の層（例えば、正孔輸送層）に到達することを阻止する。有機ＥＬ素子が、正孔輸送層を含む場合は、発光層と正孔輸送層との間に当該障壁層を含むことが好ましい。
　また、励起エネルギーが発光層からその周辺層に漏れ出さないように、障壁層を発光層に隣接させて設けてもよい。発光層で生成した励起子が、当該障壁層よりも電極側の層（例えば、電子輸送層及び正孔輸送層等）に移動することを阻止する。
　発光層と障壁層とは接合していることが好ましい。 Further, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light emitting layer. Preferably, the barrier layer is disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons.
For example, when a barrier layer is placed in contact with the emitting layer on the cathode side, the barrier layer transports electrons and holes reach the layer on the cathode side (e.g., electron transport layer) than the barrier layer. prevent you from doing When the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light emitting layer and the electron transport layer.
Furthermore, when a barrier layer is disposed in contact with the light emitting layer on the anode side, the barrier layer transports holes and electrons are transferred to a layer on the anode side (for example, a hole transport layer) than the barrier layer. prevent it from reaching. When the organic EL element includes a hole transport layer, it is preferable to include the barrier layer between the light emitting layer and the hole transport layer.
Furthermore, a barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. Excitons generated in the light emitting layer are prevented from moving to layers closer to the electrode than the barrier layer (for example, an electron transport layer, a hole transport layer, etc.).
It is preferable that the light-emitting layer and the barrier layer are bonded to each other.

　その他、本発明の実施における具体的な構造、及び形状等は、本発明の目的を達成できる範囲で他の構造等としてもよい。 In addition, the specific structure, shape, etc. in carrying out the present invention may be changed to other structures within the range that can achieve the purpose of the present invention.

　以下、実施例を挙げて本発明をさらに詳細に説明する。本発明はこれら実施例に何ら限定されない。 Hereinafter, the present invention will be explained in more detail with reference to Examples. The present invention is not limited to these examples at all.

＜化合物＞
　実施例の有機ＥＬ素子の製造に用いた、一般式（１－１）で表される化合物Ｍ３を以下に示す。 <Compound>
The compound M3 represented by the general formula (1-1) used in the production of the organic EL device of the example is shown below.

　比較例の有機ＥＬ素子の製造に用いた化合物を以下に示す。 The compounds used for manufacturing the organic EL device of the comparative example are shown below.

　実施例及び比較例に係る有機ＥＬ素子の製造に用いたその他の化合物を以下に示す。 Other compounds used in the production of organic EL devices according to Examples and Comparative Examples are shown below.

［有機ＥＬ素子の製造］
（実施例１）
　２５ｍｍ×７５ｍｍ×１．１ｍｍ厚のＩＴＯ透明電極（陽極）付きガラス基板（ジオマテック株式会社製）を、イソプロピルアルコール中で５分間超音波洗浄を行った後、ＵＶオゾン洗浄を１分間行った。ＩＴＯの膜厚は、１３０ｎｍとした。
　洗浄後の透明電極ライン付き前記ガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に透明電極を覆うようにして化合物ＨＴ－１と化合物ＨＡとを共蒸着し、膜厚１０ｎｍの正孔注入層を形成した。正孔注入層における化合物ＨＴ－１の濃度を９７質量％とし、化合物ＨＡの濃度を３質量％とした。
　次に、正孔注入層上に、化合物ＨＴ－１を蒸着し、膜厚９０ｎｍの正孔輸送層を形成した。
　次に、この正孔輸送層上に、化合物ＨＴ－２を蒸着し、膜厚３０ｎｍの電子障壁層を形成した。
　次に、この電子障壁層上に、化合物Ｍ１である蛍光発光性の化合物ＧＤ－１と、化合物Ｍ２である遅延蛍光性の化合物ＴＡＤＦ－１と、化合物Ｍ３である化合物Ｍ３－１とを共蒸着し、膜厚４０ｎｍの発光層を形成した。発光層における化合物ＧＤ－１の濃度を０．６質量％とし、化合物ＴＡＤＦ－１の濃度を２５質量％とし、化合物Ｍ３－１の濃度を７４．４質量％とした。
　次に、この発光層上に、化合物ＥＴ－１を蒸着し、膜厚５ｎｍの正孔障壁層を形成した。
　次に、この正孔障壁層上に、化合物ＥＴ－２及び化合物Ｌｉｑを共蒸着し、膜厚３５ｎｍの電子輸送層を形成した。電子輸送層における化合物ＥＴ－２の濃度を５０質量％とし、化合物Ｌｉｑの濃度を５０質量％とした。なお、Ｌｉｑは、（８－キノリノラト）リチウム（（８－Ｑｕｉｎｏｌｉｎｏｌａｔｏ）ｌｉｔｈｉｕｍ）の略称である。
　次に、この電子輸送層上に、イッテルビウム（Ｙｂ）を蒸着し、膜厚１ｎｍの電子注入性電極（陰極）を形成した。
　そして、この電子注入性電極上に、金属アルミニウム（Ａｌ）を蒸着し、膜厚８０ｎｍの金属Ａｌ陰極を形成した。
　実施例１の有機ＥＬ素子の素子構成を略式的に示すと、次のとおりである。
ITO(130)/HT-1:HA(10,97％:3%)/HT-1(90)/HT-2(30)/M3-1:TADF-1:GD-1(40,74.4%:25%:0.6%)/ET-1(5)/ET-2:Liq(35,50%:50%)/Yb(1)/Al(80)
　なお、括弧内の数字は、膜厚（単位：ｎｍ）を示す。
　同じく括弧内において、パーセント表示された数字（９７％：３％）は、正孔注入層における化合物ＨＴ－１及び化合物ＨＡの割合（質量％）を示し、パーセント表示された数字（７４．４％：２５％：０．６％）は、発光層における化合物Ｍ３、化合物Ｍ２及び化合物Ｍ１の割合（質量％）を示し、パーセント表示された数字（５０％：５０％）は、電子輸送層における化合物ＥＴ－２及び化合物Ｌｉｑの割合（質量％）を示す。 [Manufacture of organic EL elements]
(Example 1)
A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130 nm.
The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum evaporation device, and first, compound HT-1 and compound HA were added to cover the transparent electrode on the side on which the transparent electrode lines were formed. was co-evaporated to form a hole injection layer with a thickness of 10 nm. The concentration of compound HT-1 in the hole injection layer was 97% by mass, and the concentration of compound HA was 3% by mass.
Next, compound HT-1 was deposited on the hole injection layer to form a hole transport layer with a thickness of 90 nm.
Next, compound HT-2 was deposited on this hole transport layer to form an electron barrier layer with a thickness of 30 nm.
Next, on this electron barrier layer, a fluorescent compound GD-1 which is a compound M1, a delayed fluorescent compound TADF-1 which is a compound M2, and a compound M3-1 which is a compound M3 are co-evaporated. Then, a light emitting layer with a thickness of 40 nm was formed. The concentration of compound GD-1 in the light emitting layer was 0.6% by mass, the concentration of compound TADF-1 was 25% by mass, and the concentration of compound M3-1 was 74.4% by mass.
Next, compound ET-1 was deposited on this light emitting layer to form a hole blocking layer with a thickness of 5 nm.
Next, compound ET-2 and compound Liq were co-deposited on this hole blocking layer to form an electron transport layer with a thickness of 35 nm. The concentration of compound ET-2 in the electron transport layer was 50% by mass, and the concentration of compound Liq was 50% by mass. Note that Liq is an abbreviation for (8-Quinolinolato)lithium.
Next, ytterbium (Yb) was deposited on this electron transport layer to form an electron injection electrode (cathode) with a thickness of 1 nm.
Then, metal aluminum (Al) was deposited on this electron injection electrode to form a metal Al cathode with a film thickness of 80 nm.
The element structure of the organic EL element of Example 1 is schematically shown as follows.
ITO(130)/HT-1:HA(10,97%:3%)/HT-1(90)/HT-2(30)/M3-1:TADF-1:GD-1(40,74.4% :25%:0.6%)/ET-1(5)/ET-2:Liq(35,50%:50%)/Yb(1)/Al(80)
Note that the numbers in parentheses indicate the film thickness (unit: nm).
Similarly, in parentheses, the number expressed as a percentage (97%: 3%) indicates the proportion (mass%) of compound HT-1 and compound HA in the hole injection layer, and the number expressed as a percentage (74.4%) :25%:0.6%) indicates the proportion (mass%) of compound M3, compound M2, and compound M1 in the light emitting layer, and the number expressed as a percentage (50%:50%) indicates the proportion of the compound M3, compound M2, and compound M1 in the electron transport layer. The ratio (mass%) of ET-2 and compound Liq is shown.

〔実施例２～３〕
　実施例２～３に係る有機ＥＬ素子は、それぞれ、実施例１で用いた化合物Ｍ３－１を表１に記載の化合物に変更したこと以外、実施例１と同様にして作製した。 [Example 2-3]
The organic EL devices according to Examples 2 to 3 were produced in the same manner as in Example 1, except that the compound M3-1 used in Example 1 was changed to the compound listed in Table 1.

〔比較例１〕
　比較例１に係る有機ＥＬ素子は、実施例１で用いた化合物Ｍ３－１を表１に記載の化合物に変更したこと以外、実施例１と同様にして作製した。 [Comparative example 1]
An organic EL device according to Comparative Example 1 was produced in the same manner as in Example 1, except that the compound M3-1 used in Example 1 was changed to the compound listed in Table 1.

〔実施例４〕
　実施例４に係る有機ＥＬ素子は、実施例１の発光層中における化合物ＴＡＤＦ－１の濃度を表１に記載の濃度に変更し、化合物Ｍ３－１の濃度を６９．４質量％（ｗｔ％）に変更したこと以外、実施例１と同様にして作製した。 [Example 4]
In the organic EL device according to Example 4, the concentration of compound TADF-1 in the light emitting layer of Example 1 was changed to the concentration listed in Table 1, and the concentration of compound M3-1 was changed to 69.4% by mass (wt%). ) was produced in the same manner as in Example 1, except for changing.

〔実施例５～６〕
　実施例５～６に係る有機ＥＬ素子は、それぞれ、実施例４で用いた化合物Ｍ３－１を表１に記載の化合物に変更したこと以外、実施例４と同様にして作製した。 [Examples 5-6]
The organic EL devices according to Examples 5 and 6 were produced in the same manner as in Example 4, except that the compound M3-1 used in Example 4 was changed to the compound listed in Table 1.

〔比較例２〕
　比較例２に係る有機ＥＬ素子は、実施例４で用いた化合物Ｍ３－１を表１に記載の化合物に変更したこと以外、実施例４と同様にして作製した。 [Comparative example 2]
An organic EL device according to Comparative Example 2 was produced in the same manner as in Example 4, except that the compound M3-1 used in Example 4 was changed to the compound listed in Table 1.

［有機ＥＬ素子の評価］
　作製した有機ＥＬ素子について、以下の評価を行った。測定結果を表１に示す。 [Evaluation of organic EL element]
The produced organic EL device was evaluated as follows. The measurement results are shown in Table 1.

（外部量子効率ＥＱＥ）
　電流密度が１０ｍＡ／ｃｍ２となるように素子に電圧を印加した時の分光放射輝度スペクトルを分光放射輝度計ＣＳ－２０００（コニカミノルタ株式会社製）で計測した。得られた分光放射輝度スペクトルから、ランバシアン放射を行ったと仮定し外部量子効率ＥＱＥ（単位：％）を算出した。表１に「ＥＱＥ（相対値）」（単位：％）を示す。
　実施例１～３の「ＥＱＥ（相対値）」は、各例のＥＱＥの測定値、並びに下記数式（数１Ｘ）に基づいて算出した。
　実施例４～６の「ＥＱＥ（相対値）」は、各例のＥＱＥの測定値、並びに下記数式（数２Ｘ）に基づいて算出した。
　ＥＱＥ（相対値）＝（各例のＥＱＥ／比較例１のＥＱＥ）×１００…（数１Ｘ）
　ＥＱＥ（相対値）＝（各例のＥＱＥ／比較例２のＥＱＥ）×１００…（数２Ｘ） (External quantum efficiency EQE)
The spectral radiance spectrum was measured using a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to the device so that the current density was 10 mA/cm 2 . From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambassian radiation was performed. Table 1 shows "EQE (relative value)" (unit: %).
The "EQE (relative value)" of Examples 1 to 3 was calculated based on the measured value of EQE of each example and the following mathematical formula (Equation 1X).
The "EQE (relative value)" of Examples 4 to 6 was calculated based on the measured value of EQE of each example and the following formula (Equation 2X).
EQE (relative value) = (EQE of each example/EQE of comparative example 1) x 100... (Math 1X)
EQE (relative value) = (EQE of each example/EQE of comparative example 2) x 100... (Math 2X)

（最大ピーク波長λｐ）
　電流密度が１０ｍＡ／ｃｍ２となるように素子に電圧を印加した時の分光放射輝度スペクトルを分光放射輝度計ＣＳ－２０００（コニカミノルタ株式会社製）で計測した。得られた分光放射輝度スペクトルから、最大ピーク波長λｐ（単位：ｎｍ）を求めた。 (Maximum peak wavelength λp)
The spectral radiance spectrum was measured using a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to the device so that the current density was 10 mA/cm 2 . The maximum peak wavelength λp (unit: nm) was determined from the obtained spectral radiance spectrum.

（寿命ＬＴ９５）
　作製した有機ＥＬ素子に、電流密度が５０ｍＡ／ｃｍ２となるように電圧を印加し、初期輝度に対して輝度が９５％となるまでの時間（ＬＴ９５（単位：ｈｒ））を寿命として測定した。輝度は、分光放射輝度計ＣＳ－２０００（コニカミノルタ株式会社製）を用いて測定した。表１に「ＬＴ９５（相対値）」（単位：％）を示す。
　実施例１～３の「ＬＴ９５（相対値）」は、各例のＬＴ９５の測定値、並びに下記数式（数１Ｙ）に基づいて算出した。
　実施例４～６の「ＬＴ９５（相対値）」は、各例のＬＴ９５の測定値、並びに下記数式（数２Ｙ）に基づいて算出した。
　ＬＴ９５（相対値）＝（各例のＬＴ９５／比較例１のＬＴ９５）×１００…（数１Ｙ）
　ＬＴ９５（相対値）＝（各例のＬＴ９５／比較例２のＬＴ９５）×１００…（数２Ｙ） (Life span LT95)
A voltage was applied to the manufactured organic EL element so that the current density was 50 mA/cm 2 , and the time (LT95 (unit: hr)) until the brightness reached 95% of the initial brightness was measured as the life span. . The brightness was measured using a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc.). Table 1 shows "LT95 (relative value)" (unit: %).
"LT95 (relative value)" of Examples 1 to 3 was calculated based on the measured value of LT95 of each example and the following formula (Equation 1Y).
"LT95 (relative value)" of Examples 4 to 6 was calculated based on the measured value of LT95 of each example and the following formula (Equation 2Y).
LT95 (relative value) = (LT95 of each example/LT95 of comparative example 1) x 100... (Math 1Y)
LT95 (relative value) = (LT95 of each example/LT95 of comparative example 2) x 100... (Math 2Y)

（ＣＩＥ１９３１色度）
　有機ＥＬ素子の電流密度が１０ｍＡ／ｃｍ２となるように素子に電圧を印加した時のＣＩＥ１９３１色度座標（ｘ、ｙ）を分光放射輝度計ＣＳ－２０００（コニカミノルタ社製）で計測した。 (CIE1931 chromaticity)
CIE1931 chromaticity coordinates (x, y) were measured using a spectral radiance meter CS-2000 (manufactured by Konica Minolta) when a voltage was applied to the organic EL element such that the current density of the element was 10 mA/cm 2 .

Figure JPOXMLDOC01-appb-T000124
Figure JPOXMLDOC01-appb-T000124

　前記一般式（１－１）で表される化合物Ｍ３と、遅延蛍光性の化合物Ｍ２と、蛍光発光性の化合物Ｍ１と、を発光層に含む実施例１～３の有機ＥＬ素子は、前記化合物Ｍ３を化合物Ｒｅｆ－１に置き換えた比較例１の有機ＥＬ素子に比べて、高効率で発光した。
　また、前記一般式（１－１）で表される化合物Ｍ３と、遅延蛍光性の化合物Ｍ２と、蛍光発光性の化合物Ｍ１と、を発光層に含む実施例４～６の有機ＥＬ素子は、前記化合物Ｍ３を化合物Ｒｅｆ－１に置き換えた比較例２の有機ＥＬ素子に比べて、高効率で発光し、かつ寿命が長くなった。 The organic EL devices of Examples 1 to 3 include the compound M3 represented by the general formula (1-1), the delayed fluorescent compound M2, and the fluorescent compound M1 in the light emitting layer. Compared to the organic EL device of Comparative Example 1 in which M3 was replaced with compound Ref-1, it emitted light with high efficiency.
Further, the organic EL devices of Examples 4 to 6 containing the compound M3 represented by the general formula (1-1), the delayed fluorescent compound M2, and the fluorescent compound M1 in the light emitting layer, Compared to the organic EL device of Comparative Example 2 in which Compound M3 was replaced with Compound Ref-1, it emitted light with high efficiency and had a longer life.

＜化合物の評価＞
　表１中に記載した化合物の物性値は、以下の方法で測定した。 <Compound evaluation>
The physical property values of the compounds listed in Table 1 were measured by the following methods.

・化合物ＴＡＤＦ－１の遅延蛍光性
　遅延蛍光性は図２に示す装置を利用して過渡ＰＬを測定することにより確認した。前記化合物ＴＡＤＦ－１をトルエンに溶解し、自己吸収の寄与を取り除くため励起波長において吸光度が０．０５以下の希薄溶液を調製した。また酸素による消光を防ぐため、試料溶液を凍結脱気した後にアルゴン雰囲気下で蓋付きのセルに封入することで、アルゴンで飽和された酸素フリーの試料溶液とした。
　上記試料溶液の蛍光スペクトルを分光蛍光光度計ＦＰ－８６００（日本分光社製）で測定し、また同条件で９，１０－ジフェニルアントラセンのエタノール溶液の蛍光スペクトルを測定した。両スペクトルの蛍光面積強度を用いて、Ｍｏｒｒｉｓ　ｅｔ　ａｌ．　Ｊ．Ｐｈｙｓ．Ｃｈｅｍ．８０（１９７６）９６９中の（１）式により全蛍光量子収率を算出した。
　前記化合物ＴＡＤＦ－１が吸収する波長のパルス光（パルスレーザーから照射される光）で励起された後、当該励起状態から即座に観察されるＰｒｏｍｐｔ発光（即時発光）と、当該励起後、即座には観察されず、その後観察されるＤｅｌａｙ発光（遅延発光）とが存在する。本実施例における遅延蛍光発光とは、Ｄｅｌａｙ発光（遅延発光）の量がＰｒｏｍｐｔ発光（即時発光）の量に対して５％以上を意味する。具体的には、Ｐｒｏｍｐｔ発光（即時発光）の量をＸＰとし、Ｄｅｌａｙ発光（遅延発光）の量をＸＤとしたときに、ＸＤ／ＸＰの値が０．０５以上であることを意味する。
　Ｐｒｏｍｐｔ発光とＤｅｌａｙ発光の量とその比は、“Ｎａｔｕｒｅ　４９２，　２３４－２３８，　２０１２” （参考文献１）に記載された方法と同様の方法により求めることができる。なお、Ｐｒｏｍｐｔ発光とＤｅｌａｙ発光の量の算出に使用される装置は、前記参考文献１に記載の装置、または図２に記載の装置に限定されない。
　化合物ＴＡＤＦ－１について、Ｄｅｌａｙ発光（遅延発光）の量がＰｒｏｍｐｔ発光（即時発光）の量に対して５％以上であることが確認された。
　具体的には、化合物ＴＡＤＦ－１について、ＸＤ／ＸＰの値が０．０５以上であった。 - Delayed fluorescence of compound TADF-1 Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in FIG. The compound TADF-1 was dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption. In order to prevent quenching due to oxygen, the sample solution was frozen and degassed and then sealed in a cell with a lid under an argon atmosphere, resulting in an oxygen-free sample solution saturated with argon.
The fluorescence spectrum of the above sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. Using the fluorescence area intensity of both spectra, Morris et al. J. Phys. Chem. The total fluorescence quantum yield was calculated using equation (1) in 80 (1976) 969.
Prompt light emission (immediate light emission) that is observed immediately from the excited state after being excited by pulsed light (light emitted from a pulsed laser) with a wavelength that the compound TADF-1 absorbs, and prompt light emission that is immediately observed after the excitation. is not observed, but there is delayed light emission (delayed light emission) that is observed afterwards. Delayed fluorescent light emission in this embodiment means that the amount of delayed light emission (delayed light emission) is 5% or more of the amount of prompt light emission (immediate light emission). Specifically, when the amount of prompt light emission (immediate light emission) is X P and the amount of delay light emission (delayed light emission) is X D , the value of X D /X P is 0.05 or more. means.
The amount of prompt light emission and delay light emission and the ratio thereof can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference Document 1). Note that the device used to calculate the amount of prompt light emission and delay light emission is not limited to the device described in reference document 1 or the device described in FIG. 2.
For compound TADF-1, it was confirmed that the amount of delayed light emission (delayed light emission) was 5% or more of the amount of prompt light emission (immediate light emission).
Specifically, for compound TADF-1, the value of X D /X P was 0.05 or more.

・一重項エネルギーＳ１
　測定対象化合物の一重項エネルギーＳ１は、前述の溶液法により測定した。 ・Singlet energy S 1
The singlet energy S1 of the compound to be measured was measured by the solution method described above.

・７７［Ｋ］におけるエネルギーギャップＴ７７Ｋ
　測定対象化合物のＴ７７Ｋを、前述の「三重項エネルギーと７７［Ｋ］におけるエネルギーギャップとの関係」で記載したエネルギーギャップＴ７７Ｋの測定方法により測定した。また、Ｔ７７Ｋの測定結果と上記の一重項エネルギーＳ１の値からΔＳＴを確認した。
　化合物ＧＤ－１のΔＳＴは、０．４０ｅＶであった。 ・Energy gap T at 77[K] 77K
The T 77K of the compound to be measured was measured by the method for measuring the energy gap T 77K described in "Relationship between triplet energy and energy gap at 77 [K]" above. Further, ΔST was confirmed from the measurement results of T 77K and the value of the singlet energy S 1 mentioned above.
The ΔST of compound GD-1 was 0.40 eV.

・化合物の最大ピーク波長λ
　化合物の最大ピーク波長λは、以下の方法により測定した。
　測定対象となる化合物の５μｍｏｌ／Ｌトルエン溶液を調製して石英セルに入れ、常温（３００Ｋ）でこの試料の発光スペクトル（縦軸：発光強度、横軸：波長とする。）を測定した。本実施例では、発光スペクトルを日立社製の分光光度計（装置名：Ｆ－７０００）で測定した。なお、発光スペクトル測定装置は、ここで用いた装置に限定されない。発光スペクトルにおいて、発光強度が最大となる発光スペクトルのピーク波長を最大ピーク波長λとした。 ・Maximum peak wavelength λ of compound
The maximum peak wavelength λ of the compound was measured by the following method.
A 5 μmol/L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300K). In this example, the emission spectrum was measured using a spectrophotometer manufactured by Hitachi (device name: F-7000). Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum was defined as the maximum peak wavelength λ.

＜化合物の合成＞
　化合物Ｍ３－１～化合物Ｍ３－３を合成した。 <Synthesis of compounds>
Compounds M3-1 to M3-3 were synthesized.

［合成実施例１：化合物Ｍ３－１の合成］
（１－１）中間体Ｍ－１の合成 [Synthesis Example 1: Synthesis of compound M3-1]
(1-1) Synthesis of intermediate M-1

　窒素雰囲気下、３－クロロフェニルボロン酸（４．６３ｇ，２９．６ｍｍｏｌ）、２－（３－ブロモフェニル）ジベンゾ［ｂ，ｄ］フラン（９．５６ｇ，２９．６ｍｍｏｌ）、ビス（トリフェニルホスフィン）パラジウム（ＩＩ）ジクロリド（０．６２３ｇ，０．８８８ｍｍｏｌ）、及び炭酸ナトリウム（４．７１ｇ，４４．４ｍｍｏｌ）の混合物にジメトキシエタン（１５０ｍＬ）と水（３０ｍＬ）を加え、９０℃で３時間撹拌した。反応終了後、水とトルエンを加えて有機層を抽出し、飽和食塩水で洗浄した。この有機層を硫酸マグネシウムで乾燥し、ろ過後溶媒を留去した。得られた反応生成物をシリカゲル化クロマトグラフィーにより精製し、中間体Ｍ－１を得た（８．７１ｇ、収率８３％）。ＬＣ－ＭＳ（Ｌｉｑｕｉｄ　Ｃｈｒｏｍａｔｏｇｒａｐｈｙ－Ｍａｓｓ　ｓｐｅｃｔｒｏｍｅｔｒｙ）の分析により、中間体Ｍ－１と同定した。 Under nitrogen atmosphere, 3-chlorophenylboronic acid (4.63 g, 29.6 mmol), 2-(3-bromophenyl)dibenzo[b,d]furan (9.56 g, 29.6 mmol), bis(triphenylphosphine) Dimethoxyethane (150 mL) and water (30 mL) were added to a mixture of palladium (II) dichloride (0.623 g, 0.888 mmol) and sodium carbonate (4.71 g, 44.4 mmol), and the mixture was stirred at 90°C for 3 hours. . After the reaction was completed, water and toluene were added to extract the organic layer, which was washed with saturated brine. This organic layer was dried over magnesium sulfate, filtered, and then the solvent was distilled off. The obtained reaction product was purified by silica gel chromatography to obtain Intermediate M-1 (8.71 g, yield 83%). It was identified as intermediate M-1 by LC-MS (Liquid Chromatography-Mass Spectrometry) analysis.

（１－２）化合物Ｍ３－１の合成 (1-2) Synthesis of compound M3-1

　窒素雰囲気下、１２Ｈ－ベンゾ［４，５］チエノ［２，３－ａ］カルバゾール（１．７０ｇ，６．２１ｍｍｏｌ）、中間体Ｍ－１（２．１０ｇ，５．９１ｍｍｏｌ）、ジベンジリデンアセトンパラジウム（０．６８ｇ，０．１１８ｍｍｏｌ）、２－ジシクロヘキシルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル（０．１１３ｇ，０．２３６ｍｍｏｌ）、及びナトリウムｔｅｒｔ－ブトキシド（０．８５２ｇ，８．８７ｍｍｏｌ）の混合物にキシレン（３０ｍＬ）を加え、１４０℃で２時間撹拌した。反応終了後、水とトルエンを加えて有機層を抽出し、飽和食塩水で洗浄した。この有機層を硫酸マグネシウムで乾燥し、ろ過後溶媒を留去した。得られた反応生成物をシリカゲル化クロマトグラフィーにより精製し、トルエンを用いて再結晶させ、化合物Ｍ３－１を得た（０．８５ｇ、収率２４％）。ＬＣ－ＭＳの分析により、化合物Ｍ３－１と同定した。 Under nitrogen atmosphere, 12H-benzo[4,5]thieno[2,3-a]carbazole (1.70 g, 6.21 mmol), intermediate M-1 (2.10 g, 5.91 mmol), dibenzylideneacetone palladium (0.68 g, 0.118 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.113 g, 0.236 mmol), and sodium tert-butoxide (0.852 g, 8. Xylene (30 mL) was added to the mixture (87 mmol), and the mixture was stirred at 140°C for 2 hours. After the reaction was completed, water and toluene were added to extract the organic layer, which was washed with saturated brine. This organic layer was dried over magnesium sulfate, filtered, and then the solvent was distilled off. The obtained reaction product was purified by silica gel chromatography and recrystallized using toluene to obtain compound M3-1 (0.85 g, yield 24%). It was identified as compound M3-1 by LC-MS analysis.

［合成実施例２：化合物Ｍ３－２の合成］
（２－１）化合物Ｍ３－２の合成 [Synthesis Example 2: Synthesis of compound M3-2]
(2-1) Synthesis of compound M3-2

　窒素雰囲気下、５Ｈ－ベンゾフロ［３，２－ｃ］カルバゾール（１．６４ｇ，６．３８ｍｍｏｌ）、中間体Ｍ－１（２．１６ｇ，６．０８ｍｍｏｌ）、ジベンジリデンアセトンパラジウム（０．６９９ｇ，０．１２２ｍｍｏｌ）、２－ジシクロヘキシルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル（０．１１６ｇ，０．２４３ｍｍｏｌ）、及びナトリウムｔｅｒｔ－ブトキシド（０．８７７ｇ，９．１２ｍｍｏｌ）の混合物にキシレン（３０ｍＬ）を加え、１４０℃で２時間撹拌した。反応終了後、水とトルエンを加えて有機層を抽出し、飽和食塩水で洗浄した。この有機層を硫酸マグネシウムで乾燥し、ろ過後溶媒を留去した。得られた反応生成物にヘプタンを加えてろ過し、ろ物をトルエンを用いて再結晶させ、化合物Ｍ３－２を得た（０．９２ｇ、収率２６％）。ＬＣ－ＭＳの分析により、化合物Ｍ３－２と同定した。 Under a nitrogen atmosphere, 5H-benzofuro[3,2-c]carbazole (1.64 g, 6.38 mmol), intermediate M-1 (2.16 g, 6.08 mmol), dibenzylideneacetone palladium (0.699 g, 0 xylene to a mixture of (30 mL) was added and stirred at 140°C for 2 hours. After the reaction was completed, water and toluene were added to extract the organic layer, which was washed with saturated brine. This organic layer was dried over magnesium sulfate, filtered, and then the solvent was distilled off. Heptane was added to the obtained reaction product and filtered, and the filtered product was recrystallized using toluene to obtain Compound M3-2 (0.92 g, yield 26%). It was identified as compound M3-2 by LC-MS analysis.

［合成実施例３：化合物Ｍ３－３の合成］
（３－１）化合物Ｍ３－３の合成 [Synthesis Example 3: Synthesis of compound M3-3]
(3-1) Synthesis of compound M3-3

　窒素雰囲気下、１２Ｈ－ベンゾフロ［２，３－ａ］カルバゾール（１．６４ｇ，６．３８ｍｍｏｌ）、中間体Ｍ－１（２．１６ｇ，６．０８ｍｍｏｌ）、ジベンジリデンアセトンパラジウム（０．６９９ｇ，０．１２２ｍｍｏｌ）、２－ジシクロヘキシルホスフィノ－２’，４’，６’－トリイソプロピルビフェニル（０．１１６ｇ，０．２４３ｍｍｏｌ）、及びナトリウムｔｅｒｔ－ブトキシド（０．８７７ｇ，９．１２ｍｍｏｌ）の混合物にキシレン（３０ｍＬ）を加え、１４０℃で２時間撹拌した。反応終了後、固体をろ取し、メタノールで洗浄し、トルエンを用いて再結晶させ、化合物Ｍ３－３を得た（２．４５ｇ、収率７０％）。ＬＣ－ＭＳの分析により、化合物Ｍ３－３と同定した。 Under a nitrogen atmosphere, 12H-benzofuro[2,3-a]carbazole (1.64 g, 6.38 mmol), intermediate M-1 (2.16 g, 6.08 mmol), dibenzylideneacetone palladium (0.699 g, 0 xylene to a mixture of (30 mL) was added and stirred at 140°C for 2 hours. After the reaction was completed, the solid was collected by filtration, washed with methanol, and recrystallized using toluene to obtain compound M3-3 (2.45 g, yield 70%). It was identified as compound M3-3 by LC-MS analysis.

　１…有機ＥＬ素子、２…基板、３…陽極、４…陰極、５…発光層、６…正孔注入層、７…正孔輸送層、８…電子輸送層、９…電子注入層。 1... Organic EL element, 2... Substrate, 3... Anode, 4... Cathode, 5... Light emitting layer, 6... Hole injection layer, 7... Hole transport layer, 8... Electron transport layer, 9... Electron injection layer.

Claims (20)

　陽極と、
　陰極と、
　前記陽極と前記陰極との間に含まれる発光層と、を有し、
　前記発光層は、下記一般式（１－１）または（１－２）で表される化合物Ｍ３と、遅延蛍光性の化合物Ｍ２と、を含み、
　前記化合物Ｍ３と前記化合物Ｍ２とは構造が異なり、
　前記化合物Ｍ３の一重項エネルギーＳ１（Ｍ３）と、前記化合物Ｍ２の一重項エネルギーＳ１（Ｍ２）とが、下記数式（数１）の関係を満たす、
　有機エレクトロルミネッセンス素子。
　　　Ｓ１（Ｍ３）＞Ｓ１（Ｍ２）　　　（数１）


（前記一般式（１－１）及び（１－２）において、
　Ａは、下記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）のいずれかで表される基であり、
　Ｌ１及びＬ２は、それぞれ独立に、
　　単結合、又は
　　置換もしくは無置換の環形成炭素数６～５０のアリーレン基であり、
　Ｙ１は、酸素原子又は硫黄原子であり、
　Ｒ２１～Ｒ２８のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　Ｒ１００並びに、前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８は、それぞれ独立に、
　　水素原子、
　　ハロゲン原子、
　　シアノ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、
　　置換もしくは無置換の炭素数１～３０のアルキル基、
　　置換もしくは無置換の炭素数１～３０のハロゲン化アルキル基、
　　置換もしくは無置換の環形成炭素数３～３０のシクロアルキル基、
　　置換もしくは無置換の炭素数２～３０のアルケニル基、
　　置換もしくは無置換の炭素数２～３０のアルキニル基、
　　置換もしくは無置換の炭素数３～３０のアルキルシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールホスホリル基、
　　ヒドロキシ基、
　　置換もしくは無置換の炭素数１～３０のアルコキシ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリールオキシ基、
　　－Ｎ（Ｒｚ）２で表される基、
　　チオール基、
　　置換もしくは無置換の炭素数１～３０のアルキルチオ基、
　　置換もしくは無置換の環形成炭素数７～３０のアラルキル基、
　　置換ゲルマニウム基、
　　置換ホスフィンオキシド基、
　　ニトロ基、
　　置換ボリル基、又は
　　置換もしくは無置換の環形成炭素数６～３０のアリールチオ基であり、
　Ｒｚは、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、又は
　　置換もしくは無置換の炭素数１～３０のアルキル基であり、
　－Ｎ（Ｒｚ）２における２つのＲｚは、互いに同一であるか、又は異なり、
　複数のＲ１００は、互いに同一であるか、又は異なり、
　前記一般式（１－１）及び（１－２）中、＊は、Ｒ２１～Ｒ２４が結合する六員環の炭素原子のいずれか１つとの結合位置を表す。）

（前記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）において、
　Ｘ１は、酸素原子又は硫黄原子であり、
　Ｒ１１～Ｒ２０のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ１１～Ｒ２０は、それぞれ独立に、前記一般式（１－１）及び（１－２）における前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８と同義であり、＊は、結合位置を表す。） an anode;
a cathode;
a light-emitting layer included between the anode and the cathode,
The light-emitting layer includes a compound M3 represented by the following general formula (1-1) or (1-2) and a delayed fluorescent compound M2,
The compound M3 and the compound M2 have different structures,
The singlet energy S 1 (M3) of the compound M3 and the singlet energy S 1 (M2) of the compound M2 satisfy the relationship of the following formula (Equation 1),
Organic electroluminescent device.
S 1 (M3)>S 1 (M2) (Math. 1)


(In the general formulas (1-1) and (1-2),
A is a group represented by any of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
L 1 and L 2 are each independently,
A single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,
Y 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 21 to R 28 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 100 and R 21 to R 28 that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring are each independently,
hydrogen atom,
halogen atom,
cyano group,
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
Substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
Substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,
hydroxy group,
a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
-N(Rz) a group represented by 2 ,
thiol group,
a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms,
substituted germanium group,
substituted phosphine oxide group,
nitro group,
A substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
Rz is
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
-N(Rz) The two Rz in 2 are the same or different,
A plurality of R 100s are the same or different from each other,
In the general formulas (1-1) and (1-2), * represents the bonding position to any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded. )

(In the general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
X 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 11 to R 20 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 11 to R 20 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently represented by the general formulas (1-1) and (1-2). It has the same meaning as R 21 to R 28 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, and * represents a bonding position. ) 　請求項１に記載の有機エレクトロルミネッセンス素子において、
　前記化合物Ｍ３は、前記一般式（１－１）で表される化合物である、
　有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to claim 1,
The compound M3 is a compound represented by the general formula (1-1),
Organic electroluminescent device. 　請求項１または請求項２に記載の有機エレクトロルミネッセンス素子において、
　Ｌ１及びＬ２が単結合である、
　有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to claim 1 or 2,
L 1 and L 2 are single bonds,
Organic electroluminescent device. 　請求項１から請求項３のいずれか一項に記載の有機エレクトロルミネッセンス素子において、
　Ａが前記一般式（１１Ｆ）で表される基である、
　有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of claims 1 to 3,
A is a group represented by the general formula (11F),
Organic electroluminescent device. 　請求項１から請求項４のいずれか一項に記載の有機エレクトロルミネッセンス素子において、
　Ｙ１が酸素原子である、
　有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of claims 1 to 4,
Y 1 is an oxygen atom,
Organic electroluminescent device. 　請求項１から請求項５のいずれか一項に記載の有機エレクトロルミネッセンス素子において、
　Ｘ１が硫黄原子である、
　有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of claims 1 to 5,
X 1 is a sulfur atom,
Organic electroluminescent device. 　請求項１から請求項６のいずれか一項に記載の有機エレクトロルミネッセンス素子において、
　Ｒ２１～Ｒ２８が水素原子である、
　有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of claims 1 to 6,
R 21 to R 28 are hydrogen atoms,
Organic electroluminescent device. 　請求項１から請求項７のいずれか一項に記載の有機エレクトロルミネッセンス素子において、
　Ｒ１１～Ｒ２０が水素原子である、
　有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of claims 1 to 7,
R 11 to R 20 are hydrogen atoms,
Organic electroluminescent device. 　請求項１から請求項８のいずれか一項に記載の有機エレクトロルミネッセンス素子において、
　Ｒ１００が水素原子である、
　有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of claims 1 to 8,
R 100 is a hydrogen atom,
Organic electroluminescent device. 　請求項１から請求項９のいずれか一項に記載の有機エレクトロルミネッセンス素子において、
　前記発光層は、金属錯体を含まない、
　有機エレクトロルミネッセンス素子。 The organic electroluminescent device according to any one of claims 1 to 9,
The light emitting layer does not contain a metal complex,
Organic electroluminescent device. 　請求項１から請求項１０のいずれか一項に記載の有機エレクトロルミネッセンス素子を搭載した電子機器。 An electronic device equipped with the organic electroluminescent device according to any one of claims 1 to 10. 　下記一般式（１００－１）～（１００－４）のいずれかで表される化合物。




（前記一般式（１００－１）～（１００－４）において、
　Ａは、下記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）のいずれかで表される基であり、
　Ｌ１及びＬ２は、それぞれ独立に、
　　単結合、又は
　　置換もしくは無置換の環形成炭素数６～５０のアリーレン基であり、
　Ｙ１は、酸素原子又は硫黄原子であり、
　Ｒ２１～Ｒ２８のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　Ｒ１００並びに、前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８は、それぞれ独立に、
　　水素原子、
　　ハロゲン原子、
　　シアノ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、
　　置換もしくは無置換の炭素数１～３０のアルキル基、
　　置換もしくは無置換の炭素数１～３０のハロゲン化アルキル基、
　　置換もしくは無置換の環形成炭素数３～３０のシクロアルキル基、
　　置換もしくは無置換の炭素数２～３０のアルケニル基、
　　置換もしくは無置換の炭素数２～３０のアルキニル基、
　　置換もしくは無置換の炭素数３～３０のアルキルシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールシリル基、
　　置換もしくは無置換の環形成炭素数６～６０のアリールホスホリル基、
　　ヒドロキシ基、
　　置換もしくは無置換の炭素数１～３０のアルコキシ基、
　　置換もしくは無置換の環形成炭素数６～３０のアリールオキシ基、
　　－Ｎ（Ｒｚ）２で表される基、
　　チオール基、
　　置換もしくは無置換の炭素数１～３０のアルキルチオ基、
　　置換もしくは無置換の環形成炭素数７～３０のアラルキル基、
　　置換ゲルマニウム基、
　　置換ホスフィンオキシド基、
　　ニトロ基、
　　置換ボリル基、又は
　　置換もしくは無置換の環形成炭素数６～３０のアリールチオ基であり、
　Ｒｚは、
　　置換もしくは無置換の環形成炭素数６～３０のアリール基、
　　置換もしくは無置換の環形成原子数５～３０の複素環基、又は
　　置換もしくは無置換の炭素数１～３０のアルキル基であり、
　－Ｎ（Ｒｚ）２における２つのＲｚは、互いに同一であるか、又は異なり、
　複数のＲ１００は、互いに同一であるか、又は異なり、
　ただし、前記一般式（１００－４）中、Ｒ１００は、－Ｎ（Ｒｚ）２で表される基ではない。
　前記一般式（１００－４）中、＊は、Ｒ２１～Ｒ２４が結合する六員環の炭素原子のいずれか１つとの結合位置を表す。）

（前記一般式（１１Ａ）、（１１Ｂ）、（１１Ｃ）、（１１Ｄ）、（１１Ｅ）及び（１１Ｆ）において、
　Ｘ１は、酸素原子又は硫黄原子であり、
　Ｒ１１～Ｒ２０のうちの隣接する２つ以上からなる組の１組以上が、
　　互いに結合して、置換もしくは無置換の単環を形成するか、
　　互いに結合して、置換もしくは無置換の縮合環を形成するか、又は
　　互いに結合せず、
　前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ１１～Ｒ２０は、それぞれ独立に、前記一般式（１００－１）～（１００－４）における前記置換もしくは無置換の単環を形成せず、かつ前記置換もしくは無置換の縮合環を形成しないＲ２１～Ｒ２８と同義であり、＊は、結合位置を表す。） A compound represented by any of the following general formulas (100-1) to (100-4).




(In the general formulas (100-1) to (100-4),
A is a group represented by any of the following general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
L 1 and L 2 are each independently,
A single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,
Y 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 21 to R 28 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 100 and R 21 to R 28 that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring are each independently,
hydrogen atom,
halogen atom,
cyano group,
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
Substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
Substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,
hydroxy group,
a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
-N(Rz) a group represented by 2 ,
thiol group,
a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms,
substituted germanium group,
substituted phosphine oxide group,
nitro group,
A substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
Rz is
a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
-N(Rz) The two Rz in 2 are the same or different,
A plurality of R 100s are the same or different from each other,
However, in the general formula (100-4), R 100 is not a group represented by -N(Rz) 2 .
In the general formula (100-4), * represents the bonding position to any one of the carbon atoms of the six-membered ring to which R 21 to R 24 are bonded. )

(In the general formulas (11A), (11B), (11C), (11D), (11E) and (11F),
X 1 is an oxygen atom or a sulfur atom,
One or more sets of two or more adjacent ones of R 11 to R 20 are
bond to each other to form a substituted or unsubstituted monocycle,
are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,
R 11 to R 20 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring are each independently represented by the general formulas (100-1) to (100-4). It has the same meaning as R 21 to R 28 that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, and * represents a bonding position. ) 　請求項１２に記載の化合物において、
　前記一般式（１００－１）、前記一般式（１００－２）、又は前記一般式（１００－３）で表される、
　化合物。 In the compound according to claim 12,
Represented by the general formula (100-1), the general formula (100-2), or the general formula (100-3),
Compound. 　請求項１２または請求項１３に記載の化合物において、
　Ｌ１及びＬ２が単結合である、
　化合物。 In the compound according to claim 12 or claim 13,
L 1 and L 2 are single bonds,
Compound. 　請求項１２から請求項１４のいずれか一項に記載の化合物において、
　Ａが前記一般式（１１Ｆ）で表される基である、
　化合物。 The compound according to any one of claims 12 to 14,
A is a group represented by the general formula (11F),
Compound. 　請求項１２から請求項１５のいずれか一項に記載の化合物において、
　Ｙ１が酸素原子である、
　化合物。 The compound according to any one of claims 12 to 15,
Y 1 is an oxygen atom,
Compound. 　請求項１２から請求項１６のいずれか一項に記載の化合物において、
　Ｘ１が硫黄原子である、
　化合物。 The compound according to any one of claims 12 to 16,
X 1 is a sulfur atom,
Compound. 　請求項１２から請求項１７のいずれか一項に記載の化合物において、
　Ｒ２１～Ｒ２８が水素原子である、
　化合物。 The compound according to any one of claims 12 to 17,
R 21 to R 28 are hydrogen atoms,
Compound. 　請求項１２から請求項１８のいずれか一項に記載の化合物において、
　Ｒ１１～Ｒ２０が水素原子である、
　化合物。 The compound according to any one of claims 12 to 18,
R 11 to R 20 are hydrogen atoms,
Compound. 　請求項１２から請求項１９のいずれか一項に記載の化合物において、
　Ｒ１００が水素原子である、
　化合物。 The compound according to any one of claims 12 to 19,
R 100 is a hydrogen atom,
Compound.
PCT/JP2023/020460 2022-06-09 2023-06-01 Organic electroluminescent element, compound, and electronic device Ceased WO2023238769A1 (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013109045A1 (en) * 2012-01-16 2013-07-25 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2020122118A1 (en) * 2018-12-14 2020-06-18 出光興産株式会社 Organic electroluminescent element, compound, material for organic electroluminescent element, and electronic device
WO2020235558A1 (en) * 2019-05-20 2020-11-26 出光興産株式会社 Organic electroluminescent element, compound, and electronic appliance
WO2022196634A1 (en) * 2021-03-15 2022-09-22 出光興産株式会社 Organic electroluminescent element and electronic device
WO2022196749A1 (en) * 2021-03-18 2022-09-22 出光興産株式会社 Organic electroluminescent element, compound, and electronic device

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Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013109045A1 (en) * 2012-01-16 2013-07-25 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2020122118A1 (en) * 2018-12-14 2020-06-18 出光興産株式会社 Organic electroluminescent element, compound, material for organic electroluminescent element, and electronic device
WO2020235558A1 (en) * 2019-05-20 2020-11-26 出光興産株式会社 Organic electroluminescent element, compound, and electronic appliance
WO2022196634A1 (en) * 2021-03-15 2022-09-22 出光興産株式会社 Organic electroluminescent element and electronic device
WO2022196749A1 (en) * 2021-03-18 2022-09-22 出光興産株式会社 Organic electroluminescent element, compound, and electronic device

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